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Chemical Structure| 870-46-2 Chemical Structure| 870-46-2
Chemical Structure| 870-46-2

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CAS No.: 870-46-2

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Product Details of [ 870-46-2 ]

CAS No. :870-46-2
Formula : C5H12N2O2
M.W : 132.16
SMILES Code : CC(OC(NN)=O)(C)C
MDL No. :MFCD00007593
InChI Key :DKACXUFSLUYRFU-UHFFFAOYSA-N
Pubchem ID :70091

Safety of [ 870-46-2 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H228-H302-H315-H319-H335
Precautionary Statements:P210-P240-P261-P264-P270-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P330-P362-P370+P378-P403+P233-P501
Class:4.1
UN#:1325
Packing Group:Ⅲ

Calculated chemistry of [ 870-46-2 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 0
Fraction Csp3 0.8
Num. rotatable bonds 3
Num. H-bond acceptors 3.0
Num. H-bond donors 2.0
Molar Refractivity 33.37
TPSA ?

Topological Polar Surface Area: Calculated from
Ertl P. et al. 2000 J. Med. Chem.

64.35 ?2

Lipophilicity

Log Po/w (iLOGP)?

iLOGP: in-house physics-based method implemented from
Daina A et al. 2014 J. Chem. Inf. Model.

1.58
Log Po/w (XLOGP3)?

XLOGP3: Atomistic and knowledge-based method calculated by
XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry

0.18
Log Po/w (WLOGP)?

WLOGP: Atomistic method implemented from
Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.

0.38
Log Po/w (MLOGP)?

MLOGP: Topological method implemented from
Moriguchi I. et al. 1992 Chem. Pharm. Bull.
Moriguchi I. et al. 1994 Chem. Pharm. Bull.
Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.

0.38
Log Po/w (SILICOS-IT)?

SILICOS-IT: Hybrid fragmental/topological method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-1.03
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.3

Water Solubility

Log S (ESOL):?

ESOL: Topological method implemented from
Delaney JS. 2004 J. Chem. Inf. Model.

-0.57
Solubility 35.2 mg/ml ; 0.266 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (Ali)?

Ali: Topological method implemented from
Ali J. et al. 2012 J. Chem. Inf. Model.

-1.09
Solubility 10.8 mg/ml ; 0.0814 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Very soluble
Log S (SILICOS-IT)?

SILICOS-IT: Fragmental method calculated by
FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com

-0.44
Solubility 48.3 mg/ml ; 0.366 mol/l
Class?

Solubility class: Log S scale
Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly

Soluble

Pharmacokinetics

GI absorption?

Gatrointestinal absorption: according to the white of the BOILED-Egg

 High
BBB permeant?

BBB permeation: according to the yolk of the BOILED-Egg

 No
P-gp substrate?

P-glycoprotein substrate: SVM model built on 1033 molecules (training set)
and tested on 415 molecules (test set)
10-fold CV: ACC=0.72 / AUC=0.77
External: ACC=0.88 / AUC=0.94

 No
CYP1A2 inhibitor?

Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.83 / AUC=0.90
External: ACC=0.84 / AUC=0.91

 No
CYP2C19 inhibitor?

Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set)
and tested on 3000 molecules (test set)
10-fold CV: ACC=0.80 / AUC=0.86
External: ACC=0.80 / AUC=0.87

 No
CYP2C9 inhibitor?

Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set)
and tested on 2075 molecules (test set)
10-fold CV: ACC=0.78 / AUC=0.85
External: ACC=0.71 / AUC=0.81

 No
CYP2D6 inhibitor?

Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set)
and tested on 1068 molecules (test set)
10-fold CV: ACC=0.79 / AUC=0.85
External: ACC=0.81 / AUC=0.87

 No
CYP3A4 inhibitor?

Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set)
and tested on 2579 molecules (test set)
10-fold CV: ACC=0.77 / AUC=0.85
External: ACC=0.78 / AUC=0.86

 No
Log Kp (skin permeation)?

Skin permeation: QSPR model implemented from
Potts RO and Guy RH. 1992 Pharm. Res.

-6.98 cm/s

Druglikeness

Lipinski?

Lipinski (Pfizer) filter: implemented from
Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev.
MW ≤ 500
MLOGP ≤ 4.15
N or O ≤ 10
NH or OH ≤ 5

 0.0
Ghose?

Ghose filter: implemented from
Ghose AK. et al. 1999 J. Comb. Chem.
160 ≤ MW ≤ 480
-0.4 ≤ WLOGP ≤ 5.6
40 ≤ MR ≤ 130
20 ≤ atoms ≤ 70

 None
Veber?

Veber (GSK) filter: implemented from
Veber DF. et al. 2002 J. Med. Chem.
Rotatable bonds ≤ 10
TPSA ≤ 140

 0.0
Egan?

Egan (Pharmacia) filter: implemented from
Egan WJ. et al. 2000 J. Med. Chem.
WLOGP ≤ 5.88
TPSA ≤ 131.6

 0.0
Muegge?

Muegge (Bayer) filter: implemented from
Muegge I. et al. 2001 J. Med. Chem.
200 ≤ MW ≤ 600
-2 ≤ XLOGP ≤ 5
TPSA ≤ 150
Num. rings ≤ 7
Num. carbon > 4
Num. heteroatoms > 1
Num. rotatable bonds ≤ 15
H-bond acc. ≤ 10
H-bond don. ≤ 5

 1.0
Bioavailability Score?

Abbott Bioavailability Score: Probability of F > 10% in rat
implemented from
Martin YC. 2005 J. Med. Chem.

0.55

Medicinal Chemistry

PAINS?

Pan Assay Interference Structures: implemented from
Baell JB. & Holloway GA. 2010 J. Med. Chem.

0.0 alert
Brenk?

Structural Alert: implemented from
Brenk R. et al. 2008 ChemMedChem

2.0 alert: heavy_metal
Leadlikeness?

Leadlikeness: implemented from
Teague SJ. 1999 Angew. Chem. Int. Ed.
250 ≤ MW ≤ 350
XLOGP ≤ 3.5
Num. rotatable bonds ≤ 7

 No; 1 violation:MW<1.0
Synthetic accessibility?

Synthetic accessibility score: from 1 (very easy) to 10 (very difficult)
based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties,
trained on 12'782'590 molecules and tested on 40 external molecules (r2 = 0.94)

 1.76

Application In Synthesis of [ 870-46-2 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 870-46-2 ]

[ 870-46-2 ] Synthesis Path-Downstream   1~29

  • 1
  • [ 7137-97-5 ]
  • [ 870-46-2 ]
  • [ 681261-72-3 ]
  • 2
  • [ 870-46-2 ]
  • [ 38430-55-6 ]
  • [ 870822-87-0 ]
YieldReaction ConditionsOperation in experiment
68.3% With acetic acid; In toluene; at 80℃; A solution of tert-butyl carbazate (14.0 g, 106.1 mmol) andcompound 2 (13.6 g, 70.8 mmol) in toluene (120 mL) with catalyticHOAc was stirred at 80 C overnight. tert-Butyl-2-{1-[4-(ethoxycarbonyl)phenyl]-ethylidene}hydrazine carboxylate was collectedby filtration as a crystalline solid (14.8 g, 68.3%). Without furtherpurification, NaBH3CN (3.3 g, 53.1 mmol) and tert-butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethylidene}-hydrazinecarboxylate (14.8g, 48.3 mmol) were dissolved in THF (120 mL). A solution of ptoluenesulfonicacid (9.7 g, 56.5 mmol) in THF (50 mL) was slowlyadded for 3 h and the reaction was detected by TLC. The mixturewas extracted with EtOAc and washed with brine, dried over anhydrousNa2SO4 and concentrated to give a white solid. The solid wasredissolved in DCM and washed with 1 N NaOH and the organiclayer was washed with 1 N HCl and brine, dried over Na2SO4 andconcentrated to yield white solid. Flash column chromatographypetroleum ether/ethyl acetate = 4/1 to yield 13.6 g (91%) tert-butyl2-{1-[4-(ethoxycarbonyl)-phenyl]ethyl}hydrazine carboxylate. 1HNMR (400 MHz, DMSO-d6) d 8.17 (s, 1H), 7.89 (d, J = 8.3 Hz, 2H),7.47 (d, J = 8.2 Hz, 2H), 4.73 (s, 1H), 4.30 (q, J = 7.1 Hz, 2H), 4.17(s, 1H), 1.33 (d, J = 6.2 Hz, 9H), 1.30 (d, J = 7.1 Hz, 3H), 1.18 (d, J =6.6 Hz, 3H). MS (ESI, m/z): 307.1 [MH].
65.7% With acetic acid; In toluene; at 80℃; A solution of tert-butyl carbazate(5.5 g, 41.6 mmol) and ethyl 4-acetylbenzoate (10 g, 52.0 mmol) intoluene (60 mL) with catalytic HOAc was stirred at 80 C overnight.tert-Butyl-2-{1-[4-(ethoxycarbonyl)phenyl]-ethylidene}hydrazinecarboxylate separated as a crystalline solid (10 g, 65.7%) and wascollected by filtration. NaBH3CN (2.4 g, 38.2 mmol) and tert-butyl2-{1-[4-(ethoxycarbonyl)phenyl]ethylidene}-hydrazinecarboxylate(10 g, 32.6 mmol) were dissolved in THF (100 mL). A solutionof p-toluene sulfonic acid (4.3 g, 22.6 mmol) in THF (25 mL) wasslowly added. After stirring the reaction for 3 h, the mixture wasextracted with EtOAc and washed with brine, dried (Na2SO4), andconcentrated to give a white solid. The solid was separated andwashed with 1 N HCl twice and brine twice, dried (Na2SO4), andconcentrated. Product precipitated as white solid and was washedwith petroleum ether/ethyl acetate (4:1) to yield 5.6 g (55.6%) oftert-butyl 2-{1-[4-(ethoxycarbonyl)-phenyl]ethyl}hydrazine carboxylate.1H NMR (400 MHz, CDCl3) d 8.01 (d, J = 8.3 Hz, 2H),7.41 (d, J = 8.3 Hz, 2H), 4.37 (q, J = 7.1 Hz, 2H), 4.22 (d, J = 6.4 Hz,1H), 1.41 (d, J = 2.7 Hz, 9H), 1.38 (d, J = 7.1 Hz, 3H), 1.35 (d,J = 6.6 Hz, 3H). MS (ESI, m/z): 307.1 [MH].
In toluene; at 80℃; for 15h; A solution of tert-butyl carbazate (13.90 g, 105 mmol) and ethyl 4-acetylbenzoate (20.00 g, 0.104 mol) in toluene (120 mL) was stirred at 80 C. overnight (15 h). tert-butyl-2-{1-[4-(ethoxycarbonyl)phenyl]ethylidene}hydrazinecarboxylate separated as crystalline solid and was collected by filtration of the mixture. HPLC/MS: m/z=307.3 (M+1)+, Rt=3.47 min. 1H NMR (500 MHz, CDCl3): delta 8.05 (2H, d, J=8.5 Hz), 7.88 (2H, d, J=8.5 Hz), 7.79 (1H, br s), 4.41 (2H, q, J=7.0 Hz), 2.24 (3H, s), 1.58 (9H, s), 1.43 (3H, t, J=7.0 Hz).
In toluene; at 80℃; for 15h; A solution of tert-butyl carbazate (13.90 g, 105 mmol) and ethyl 4-acetylbenzoate (20.00 g, 0.104 mol) in toluene (120 mL) was stirred at 80 0C overnight (15 h). tert-butyl-2-{ l-[4- (ethoxycarbonyl)phenyl]ethylidene}hydrazinecarboxylate separated as crystalline solid and was collected by filtration of the mixture. HPLC/MS: m/z = 307.3 (M+l)+, R1 = 3.47 min. 1H NMR (500 MHz, CDCl3): delta 8.05 (2H, d, J = 8.5 Hz), 7.88 (2H, d, J = 8.5 Hz), 7.79 (IH, br s), 4.41 (2H, q, J = 7.0 Hz), 2.24 (3H, s), 1.58 (9H, s), 1.43 (3H, t, J = 7.0 Hz).
In toluene; at 80℃; for 15h; Step A tert-Butyl 2-{1-[4-(ethoxycarbonyl)phenyl]ethylidene}hydrazinecarboxylate.; A solution of tert-butyl carbazate (13.90 g, 105 mmol) and ethyl 4-acetylbenzoate (20.00 g, 104 mmol) in toluene (120 mL) was stirred at 80 C. overnight (15 h). The title compound separated as crystalline solid and was collected by filtration of the mixture. HPLC/MS: m/z=307.3 (M+1)+, Rt=3.47 min. 1H NMR (500 MHz, CDCl3): delta 8.05 (d, J=8.5 Hz, 2H), 7.88 (d, J=8.5 Hz, 2H), 7.79 (br s, 1H), 4.41 (q, J=7.0 Hz, 2H), 2.24 (s, 3H), 1.58 (s, 9H), 1.43 (t, J=7.0 Hz, 3H).

  • 3
  • [ 870-46-2 ]
  • [ 2991-28-8 ]
  • [ 1079843-62-1 ]
YieldReaction ConditionsOperation in experiment
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;dmap; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 3h; To a solution of 5.Og (31.6 mmol) of <strong>[2991-28-8]2,5-difluorobenzoic acid</strong> (1-1) in 2OmL of 1: 1 THF/DMF was added 4.39g (33.2 mmol) of t-butylcarbazate, 6.67g (34.8 mmol) of EDCI, and 50 mg of DMAP. After stirring for 3h at room temperature, the reaction was dumped into ice water and extracted three times with ether. The combined organic phases were washed two times with 10percent citric acid, two times with saturated NaHCO3, once with water, once with brine, and then dried over MgSO4. Concentration by rotary evaporation provided the BOC-protected acyl hydrazine as a white solid. To a solution of 1.5g (5.5 mmol) of this material in 20 mL of CH2Cl2, cooled to 00C, was added 10 mL of trifluoroacetic acid, and the resultant mixture was allowed to stir for 2 h at that temperature. The volatiles were removed by rotary evaporation, the residue was partitioned between EtOAc and aqueous NaHCO3, the layers were separated, and the aqueous phase was extracted two more times with EtOAc. The combined organic phases were washed twice with saturated NaHCO3, brine, dried over Na2SO4, and concentrated to provide 663mg (3.85 mmol) of 2,5-difluorobenzohydrazide (1-2) as a white solid. This material was dissolved in 30 mL of EtOH, and then 1.5 mL of HOAc was added, followed by 390 muL (3.85 mmol) of benzaldehyde. After stirring for Ih at room temperature, the solvents were removed by rotary evaporation, and the residue was triturated with Et2O to provide the imine as a white powder. A portion of this imine (225mg, 0.86 mmol) was dissolved in 3 mL of acetic anhydride and heated at 125 0C for 2h After cooling to room temperature, the volatiles were removed by rotary evaporation, the residue was dissolve in EtOAc, washed twice with saturated NaHCO3, water, dried over Na2SO4, and concentrated. The residue was then purified by column chromatography with a gradient of EtOAc in hexanes to provide (1-3) as a white solid. IH NMR (500 MHz, CDC13): delta 7.6 -7.4 (m, 6H), 7.2 (m, 2H), 7.1 (s, IH), 2.4 (s, 3H) ppm. HRMS (ES) calc'd M + H for C16H12F2N2O2: 303.0940; found 303.0926.
With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride;dmap; In tetrahydrofuran; N,N-dimethyl-formamide; for 16h; Step B: Preparation of <strong>[2991-28-8]2,5-difluorobenzoic acid</strong> hydrazide: To a solution of<strong>[2991-28-8]2,5-difluorobenzoic acid</strong> (3.5 g, 22 mmol) in THF/DMF (20 mL/20 mL) was added EDCI (4.7 g, 24 mmol), DMAP (50 mg) and NH2NHBoC (3.07 g, 23.2 mmol). After stirring for 16 hours, the reaction was quenched with water (30 mL) and diluted with EtOAc (30 mL). The organic layer was then washed with HCl (0.5 M, 20 mL), saturated NaHCO3 (20 mL), and brine (20 mL). The organic layer was then dried over Na2SO4, filtered and concentrated under reduced pressure to afford the crude Boc-protected product, which was then dissolved in DCM (60 mL) at 0 °C. TFA (50 mL) was added to the above DCM solution. After stirring for 2 hours, the reaction mixture was concentrated and the residue was dissolved in DCM (60 mL). The solution was washed with saturated NaHCO3 (40 mL) and dried over Na2SO4, filtered and concentrated under reduced pressure to afford the desired crude product.
  • 4
  • [ 29006-02-8 ]
  • [ 870-46-2 ]
  • [ 25952-53-8 ]
  • [ 374889-93-7 ]
YieldReaction ConditionsOperation in experiment
57% In pyridine; ethyl acetate; (1) Carbazic acid tert-butyl ester (9.21 g) was dissolved in pyridine (120 ml), followed by addition of <strong>[29006-02-8]4-methoxybutyric acid</strong> (9.06 g) and 1-ethyl-3-(3-dimethylaminopropyl) carbodiimide hydrochloride salt (20.0 g), and stirred at ambient temperature for 64 hours. After the reaction solution was concentrated under reduced pressure, ethyl acetate was added to the residue, which was then washed with aqueous 1 mol/liter hydrochloric acid solution, saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium chloride, and dried over anhydrous sodium sulfate. After the solvent was evaporated under reduced pressure, N'-(4-methoxybutyryl) hydrazine carboxylic acid tert-butyl ester was obtained in yellow oil (9.30 g, 57%). The physico-chemical values are as follows. 1H-NMR (DMSO-d6) delta: 1.39 (9H, s), 1.65-1.78 (2H, m), 2.07-2.12 (2H, m), 3.21 (3H, s), 3.30-3.34 (2H, m), 8.64 (1H, s), 9.46 (1H, s).
  • 5
  • [ 389602-62-4 ]
  • [ 870-46-2 ]
  • [ 68957-94-8 ]
  • [ 389601-21-2 ]
YieldReaction ConditionsOperation in experiment
46% With 4-methyl-morpholine; In dichloromethane; EXAMPLE 16 N-tert.butoxycarbonylamino-3-(4'-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid amide Prepared analogously to Example 7 from 3-(4'-trifluoromethylbiphenyl-2-carbonylamino)-benzoic acid and tert.butyl hydrazinoformate in dichloromethane with the addition of propanephosphonic acid cycloanhydride and N-methylmorpholine. Yield:46% of theory Rf value:0.58 (silica gel; dichloromethane/ethanol=9:1)
  • 6
  • [ 870-46-2 ]
  • [ 143879-80-5 ]
  • [ 1073973-12-2 ]
YieldReaction ConditionsOperation in experiment
22% With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 100℃; for 3h; <strong>[143879-80-5]2,3,4-<strong>[143879-80-5]trifluorobenzonitrile</strong></strong> (3 g, 19 mmol), tert-butyl carbazate (4 g, 30 mmol) and Hunig's base were dissolved in dioxane (10 mL) and heated at 100° C. for 3 d. The mixture was concentrated and then partitioned between toluene (25 mL) and water (29 mL). The toluene layer was added to a column and chromatographed (silica gel, 10 to 40percent ethyl acetate in hexanes) to give product as an oil. Recrystallization from ethyl acetate/hexanes gave N'-(4-cyano-2,3-difluoro-phenyl)-hydrazinecarboxylic acid tert-butyl ester (1.16 g, 22percent) as a white powder. A second crop (0.5 g, 10percent) was obtained as a slightly pinkish powder. LCMS (m/z): M+H=170.1 (loss of BOC).
  • 7
  • [ 943541-20-6 ]
  • [ 870-46-2 ]
  • [ 1093204-33-1 ]
YieldReaction ConditionsOperation in experiment
33% Example 13: A route to prepare compound (I)6-{difluoror6-(1-methvl-1 H-pvrazol-4-vl)? ,2,41triazolor4,3-lpvridazin-3-vnmethvl>quinolineStep 1 : tert-butyl 2-f6-(1-methyl-1 H-pyrazol-4-yl)pyridazin-3-vnhvdrazinecarboxylatetert-butyl carbazate, 8,98g (67,3 mmol) and 3-chloro-6-(1-methyl-1 /-/-pyrazol-4- yl)pyridazine (11 ,9 g, 61 ,1 mmol) were mixed in 1-butanol (245 ml_). This mixture was heated till 900C and stirred at that temperature for 16h. The reaction mixture was cooled and water (250 ml_) and ethylacetate (250 mL) were added. The biphasic mixture was neutralised with sodium hydrogencarbonate till the pH is 7. Then the organic layer was separated and the water layer was extracted with ethylacetate (250 mL). The combined organic layers were washed once with water (250 mL) and evaporated. The residue was stirred in isopropylether, filtered off and dried under vacuum. Yield: 5,9 g (20,3 mmol; 33%) of the title compound.
  • 8
  • [ 870-46-2 ]
  • [ 4385-76-6 ]
  • [ 1160395-83-4 ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 1h; 4-Pyridin-4-yl benzoic acid (250mug, 1.25mmol), EDAC (288mug, 1.51 mmol), HOBt (227mug), and 1 ,1-dimethylethyl hydrazinecarboxylate (199mug), in DMF were stirred at <n="29"/>room temperature for 1 h. The reaction mixture was diluted with water (20mul), extracted with ethyl acetate (30mul x 3), the organic phase washed with bicarbonate, dried over magnesium sulfate and evaporated to give an oil, 520mg. This was used without further purification.
  • 9
  • [ 870-46-2 ]
  • [ 437-86-5 ]
  • [ 1075282-02-8 ]
YieldReaction ConditionsOperation in experiment
80% In dimethyl sulfoxide; at 100℃; for 0.166667h;Microwave irradiation; Stage 1: tert-butyl N-(2-methyl-6-nitro-phenyl)-hydrazino-carboxylate To 250 mg of 2-fluoro-3-methyl-nitrobenzene in 5 mL of DMSO are added 1.065 g of commercial tert-butoxycarbonylhydrazine (5 equivalents). The whole is brought to 100° C. for 10 min under microwave heating. The medium is hydrolyzed and then extracted with ethyl acetate several times. The organic phases are collected, dried on magnesium sulfate, filtered and evaporated under reduced pressure leading to a residue which is purified by chromatography on silica gel (cyclohexane/ethyl acetate: 80/20). 342 mg of product corresponding to the expected product are obtained. Yield: 80percent 1H NMR (CDCl3, 250 MHz) delta (ppm): 7.86 (d, 1H), 7.35 (d, 1H), 6.97 (t, 1H), 6.40 (s broad, 1H), 1.34 (s broad, 9H)
  • 10
  • [ 870-46-2 ]
  • [ 65632-62-4 ]
  • [ 439292-93-0 ]
  • 11
  • [ 870-46-2 ]
  • [ 149437-76-3 ]
  • [ 1235493-23-8 ]
YieldReaction ConditionsOperation in experiment
In tetrahydrofuran; at 50℃; for 16h; A mixture of tert-butyl hydrazinecarboxylate (1.45 g, 11.0 mmol) and <strong>[149437-76-3]5-(4-fluorophenyl)-5-oxopentanoic acid</strong> (2.1 g, 10 mmol) in THF (20 mL) was stirred at 50 0C for 16 h. The reaction mixture was concentrated in vacuo to afford 5-(2-(tert-butoxycarbonyl)hydrazono)-5-(4-fluorophenyl)pentanoic acid (3.2 g, 9.87 mmol, 99 % yield). LC-MS (M+H)+ 325.24. The crude product was used for subsequent chemistry without purification.
  • 12
  • [ 3973-08-8 ]
  • [ 870-46-2 ]
  • [ 1254073-60-3 ]
YieldReaction ConditionsOperation in experiment
1 ,3-thiazole-4-carboxylic acid (0.775 g, 6 mmol, commercially available from e.g. Sigma-AIdrich, Apollo or Fluorochem) was dissolved in dichloromethane (DCM) (50 ml_), and the solution was cooled to 0 0C. To this was added oxalyl chloride (0.578 ml_, 6.60 mmol) and 5 drops of DMF (cat.) and the solution was stirred, under argon, for 3 hours. The solvent was then removed in vacuo, and the remaining residue was redissolved in dichloromethane (DCM) (50 ml_), before 1 ,1-dimethylethyl hydrazinecarboxylate (0.872 g, 6.60 mmol) and DIPEA (1.258 ml_, 7.20 mmol) were added. The solution was stirred under argon for 2 hours, LCMS and TLC confirmed product formation, thus the solvent was evaporated in vacuo. The remaining residue was then partitioned between ethyl acetate (30 mL) and saturated sodium bicarbonate solution (20 ml). The aqueous phase was then further extracted with ethyl acetate (2 x 30 mL) and the combined extracts were washed with brine (30 mL), and dried over anhydrous sodium sulfate. The solvent was then evaporated in vacuo to yield the product in 1.308 g.
  • 13
  • [ 14190-59-1 ]
  • [ 870-46-2 ]
  • [ 1254073-54-5 ]
YieldReaction ConditionsOperation in experiment
EDC (742 mg, 3.87 mmol) and HOBt (593 mg, 3.87 mmol) were added to a suspension of 1 ,3-<strong>[14190-59-1]thiazole-2-carboxylic acid</strong> (500 mg, 3.87 mmol) in dry Dichloromethane (DCM) (19 ml) - solution became clear after the addition of EDC. The mixture was stirred at room temperature for 30 mins. 1 ,1-dimethylethyl hydrazinecarboxylate (512 mg, 3.87 mmol) was added and the resulting mixture was stirred at room temperature 1 day. The reaction mixture was diluted in DCM (150 mL) and washed with sat. NaHCOo (2 x 25 mL) and brine (25 mL). The resulting organic layer was dried over MgSpsi4 and concentrated under reduced pressure. The crude product was purified by flash chromatography (10percent MeOH in DCM / DCM - 10CV) to afford desired product in 432.9 mg as an orange oil. LCMS m/z 243.9 [M+H] (at) 0.66 min (2 min run)
  • 14
  • [ 61291-21-2 ]
  • [ 870-46-2 ]
  • [ 1254073-91-0 ]
YieldReaction ConditionsOperation in experiment
A solution of 5-methyl-1 ,3-thiazole-2-carboxylic acid (500 mg, 3.49 mmol) in dry dichloromethane (DCM) (17.500 ml) was stirred at room temperature under an atmosphere of argon. EDC (803 mg, 4.19 mmol) and HOBT (267 mg, 1.746 mmol) were added to the stirred solution. After 15 minutes, 1 ,1-dimethylethyl hydrazinecarboxylate (554 mg, 4.19 mmol) was added to the stirred solution. The resulting solution was stirred for 18 hours. After this time, the solution was diluted with DCM (approx. 50ml) and washed with water (2 x approx. 20ml). The organic extracts were dried over MgSO4, filtered and concentrated under reduced pressure to give a yellow coloured oil of desired product in 451 mg. LCMS m/z 257.93 [M+H] (at) 0.79 min (2 min run).
  • 15
  • [ 870-46-2 ]
  • [ 402-69-7 ]
  • [ 1254073-98-7 ]
YieldReaction ConditionsOperation in experiment
6-Fluoro-2-pyridinecarboxylic acid (2.83 g, 20.06 mmol, CAS[402-69-7], commercially available e.g. from Sigma-Aldrich or Apollo Scientific) was dissolved inDichloromethane (DCM) (100 ml.) at 0 0C. Oxalyl chloride (2.107 ml_, 24.07 mmol) and a drop of Lambda/,Lambda/-dimethylformamide (DMF) was added and the mixture was stirred for 2 hours. The solvents were removed in vacuo and azeotroped with toluene (3x20ml). The residue was dissolved in dichloromethane (DCM) (100 ml) whereupon 1 ,1-dimethylethyl hydrazinecarboxylate (2.92 g, 22.06 mmol) and Lambda/,Lambda/-diisopropylethylamine (DIPEA) (7.71 ml_, 44.1 mmol) were added. The mixture was stirred at room temperature for 3 hours and concentrated in vacuo. The residue was partitioned between ethyl acetate (100 ml) and saturated sodium bicarbonate solution (50 ml). The aqueous phase was extracted with ethyl acetate (3x100ml), the combined organic extracts were washed with brine (50 ml), were dried over anhydrous sodium sulphate and were concentrated in vacuo. The residue was purified by flash chromatography (Biotage SP4, 40+M, 0-100percent ethyl acetate/iso- hexane) to afford 1 ,1-dimethylethyl 2-[(6-fluoro-2- pyridinyl)carbonyl]hydrazinecarboxylate (5.04 g, 19.75 mmol).LC/MS = 156 (M+H-BOC)+, retention time = 0.81 minutes (2 minute method).
  • 16
  • [ 22929-52-8 ]
  • [ 870-46-2 ]
  • [ 158020-60-1 ]
YieldReaction ConditionsOperation in experiment
95% In methanol; at 15℃; for 2h; A solution of <strong>[22929-52-8]dihydrofuran-3(2H)-one</strong> (5.0 g, 58 mmol) and tert-butyl hydrazinecarboxylate (7.68 g, 58.08 mmol) in MeOH (50 mL) was stirred at 15° C. for 2 hours. The mixture was concentrated to remove MeOH and afford tert-butyl 2-(dihydrofuran-3(2H)-ylidene)hydrazine-1-carboxylate (11 g, 55 mmol, 95percent yield). 1H NMR (MeOD 400 MHz): delta4.19 (s, 2H), 4.03 (t, J=6.8 Hz, 2H), 2.53 (t, J=7.2 Hz, 2H), 1.50 (s, 9H).
85% In methanol; at 20℃; for 2h; General procedure: A 100 mL 3-neck flask with inert gas valve and septum was charged with (6.50 g, 49.04 mmol) tert-butylhydrazinecarboxylate and 30 mL MeOH. (4.91 g, 49.04 mmol) dihydro-2H-pyran-3(4H)-one was syringed into the flask. The mixture was stirred at rt for 2 h to observe the disappearance of tert-butylhydrazinecarboxylate monitored by LC-MS. The mixture was then dried over Na2SO4 and the solution was filtered and the solvent removed under reduced pressure to yield 10.4 g of white solid (99percent yield). The compound was further purified by passing through a short silica pad using 50percent EtOAc in hexanes.
27.3 g In methanol; at 10 - 35℃; for 12h; (1) Synthesis of t-butyl 2-[dihydrofuran-3(2H)-ylidene]hydrazinecarboxylate 3-oxotetrahydrofuran (10.38 g) was dissolved in methanol (200 mL), and t-butyl carbazate (17.53 g) was added to the solution. The mixture was stirred at room temperature for 12 hours. The reaction mixture was concentrated to give the title compound (27.3 g). 1H-NMR (400 MHz, CDCl3) delta (ppm): 1.52 (s, 9H), 2.46 (t, J=6.9 Hz, al), 4.10 (t, J=6.9 Hz, 2H), 4.33 (s, 2H).
1.95 mmol In ethanol;Reflux; To a solution of dihydro(3(2H)-furanone (1 .95 mmol) in ethanol(2 mL) was added tert-butyl carbazate (2.35 mmol) and the reaction was heated to reflux and stirred overnight. Volatiles were removed under reduced pressure to give the titled compound (1.95 mmol) as a white solid. 1H NMR (400 MHz,CDCI3, 3, mixture of isomers): 7.25 (5, 0.75H), 7.12 (5, 0.25 H), 4.34 (t, J= 1.2 Hz, i.5H), 4.24 (t, J=1.2 Hz, 0.5H), 4.12 (t, J = 6.9 Hz, 1 .5H), 4.02 (t, J = 6.9 Hz, 0.5H), 2.78 (td, J = 6.9, 1.2 Hz, 0.5H), 2.48 (td, J = 6.9, 1.2 Hz, 1 .5H), 1.54 (5, 7.5H), 1.53 (5, 1 .5H).

  • 18
  • [ 870-46-2 ]
  • [ 1246616-66-9 ]
  • [ 1246616-89-6 ]
YieldReaction ConditionsOperation in experiment
72.9% With acetic acid; In toluene; at 65℃; for 5h; Example 10 First StepCompound 1D (318.3 mg, 1.0 mmol) and acetic acid (0.023 mL, 0.4 mmol) were dissolved in toluene (2 mL), a solution of tert-butylcarbazate (132.3 mg, 1.0 mmol) in toluene (2 mL) was added dropwise at 65 C., and the mixture was stirred at 65 C. for 5 hours. Saturated sodium bicarbonate water was added to the reaction solution, followed by extraction with ethyl acetate. The organic layer was washed with saturated sodium chloride water, and dried with anhydrous magnesium sulfate. The solvent was distilled off, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=50:50?33:67) to obtain 315.3 mg (yield 72.9%) of Compound 10B.1H-NMR (DMSO-d6) delta: 1.36 (9H, s), 3.84 (6H, s), 5.11 (2H, s), 7.34-7.38 (5H, m), 8.33 (1H, s), 11.11 (1H, br s).
  • 19
  • [ 870-46-2 ]
  • [ 119072-55-8 ]
  • [ 19230-50-3 ]
  • [ 78-84-2 ]
  • [ 1373025-47-8 ]
YieldReaction ConditionsOperation in experiment
77% General procedure: To 292 mg (4 mmol) of isobutyraldehyde in 4 ml of MeOH, 530 mg (4 mmol)of tert-butylcarbazatare added and the mixture is stirred at rt for 2 h. Then 1011 mg (4 mmol) of o-iodobenzoic acid and 339 mg (4 mmol) of tert-butylisocyanidare added and the reaction mixture is stirred overnight at rt. After evaporation of the solvent the crude product is purified by column chromatography on silica gel (chloroform/methanol = 99.5/0.5?90/10, Rf = 0.20 [chloroform/methanol = 99.5/0.5]) to yield 1.52 g of the title compound (white solid, 73%).
  • 20
  • [ 870-46-2 ]
  • [ 119072-55-8 ]
  • [ 54413-93-3 ]
  • [ 78-84-2 ]
  • [ 1373025-40-1 ]
YieldReaction ConditionsOperation in experiment
95% General procedure: To 292 mg (4 mmol) of isobutyraldehyde in 4 ml of MeOH, 530 mg (4 mmol)of tert-butylcarbazatare added and the mixture is stirred at rt for 2 h. Then 1011 mg (4 mmol) of o-iodobenzoic acid and 339 mg (4 mmol) of tert-butylisocyanidare added and the reaction mixture is stirred overnight at rt. After evaporation of the solvent the crude product is purified by column chromatography on silica gel (chloroform/methanol = 99.5/0.5-->90/10, Rf = 0.20 [chloroform/methanol = 99.5/0.5]) to yield 1.52 g of the title compound (white solid, 73percent).
  • 21
  • [ 94201-40-8 ]
  • [ 870-46-2 ]
  • ([(tert-butoxy)carbonyl]amino}amino)(1-phenylpiperidin-4-yl)methanone [ No CAS ]
  • 22
  • [ 872422-15-6 ]
  • [ 870-46-2 ]
  • C15H18BrFN2O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 20℃; A solution of the compound (26.55 g, 102.5 mmol) obtained in Example 14-3), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (21.6 g, 112.7 mmol), 1-hydroxybenzotriazole monohydrate (17.26 g, 112.7 mmol), triethylamine (42.9 mL, 307 mmol), and tert-butoxycarbonylhydrazide (16.3 g, 123 mmol) in N,N-dimethylformamide (400 mL) was stirred overnight at room temperature. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution and then dried with anhydrous sodium sulfate. After filtration, the filtrate was concentrated under reduced pressure. A 4 M solution (60 mL) of hydrochloric acid in 1,4-dioxane and methanol (300 mL) were added to the obtained partially purified product, and the mixture was stirred at room temperature for 6.5 h. The reaction mixture was concentrated under reduced pressure, dichloromethane was added to the residue, and the organic layer was washed with saturated aqueous sodium hydrogencarbonate and saturated sodium chloride solution and then dried with anhydrous sodium sulfate. The filtrate was concentrated under reduced pressure, hexane was added to the obtained partially purified product, and the solid was collected by filtration to obtain the title compound (11.6 g, 42%) as a colorless solid. 1H-NMR (400 Hz, CDCl3) delta: 1.06 (2H, m), 1.68 (2H, m), 3.60-3.68 (2H, m), 6.53 (1H, m), 7.21-7.33 (3H, m)
  • 23
  • [ 870-46-2 ]
  • [ 582-80-9 ]
  • tert-butyl 2-(4-benzamidobenzoyl)hydrazinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
97% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In tetrahydrofuran; N,N-dimethyl-formamide; at 20℃; for 18h; The p-benzamido-benzoic acid (0.325 g, 1.3 mmol, 1.0 equiv.) and tert-butyl carbazate (0.160 g, 1.2 mmol, 0.9 equiv.) were dissolved in 6 ml of 1:1 DMF:THF at room temperature. The EDCI (0.284 g, 1.5 mmol, 1.1 equiv.) was added followed by catalytic amount of DMAP. The reaction was stirred for 18 hrs. The reaction was poured into saturated bicarb and the aqueous solution was extracted with EtOAc (3x). The combined organic layers were washed with H2O, 10percent HCl, H2O, brine, dried over Na2SO4 and concentrated in vacuo. tert-butyl 2-(4-benzamidobenzoyl) hydrazinecarboxylate (0.465 g, 1.31 mmol) was obtained as an off-white in 97percent yield.1H-NMR (400 MHz; DMSO-d6): delta 10.48 (s, 1H), 10.10 (s, 1H), 8.86 (s, 1H), 7.96 (dd, J = 8.3, 1.4 Hz, 2H), 7.90-7.85 (m, 4H), 7.63-7.59 (m, 1H), 7.56-7.53 (m, 2H), 1.43 (s, 9H); 13C NMR (101 MHz; DMSO-d6): delta 165.9, 165.4, 155.6, 142.2, 134.7, 131.8, 128.4, 128.1, 127.7, 119.5, 79.1, 28.10, 28.07; LC/MS (APCI) m/z calcd. for C19H20N3O4 [M?H]?: 354.2, found: 354.0
  • 24
  • [ 870-46-2 ]
  • [ 147905-77-9 ]
  • tert-butyl 2-(trans-4-(ethoxycarbonyl)-4-methylcyclohexyl)hydrazinecarboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% To a mixture of compound D2-3 (30 g, 163.0 mmol) and tert-butylhydrazine carboxylate (21.5 g, 163.0 mmol) in isopropanol (200 mL) was added and AcOH (catalytic amount) and the mixture was stirred at room temperature for 2 h. Upon completion of imine formation (monitored by TLC), the mixture was cooled to 0 C, and solid NaBH3CN (30.7 g, 489.1 mmol) was added in portions. The pH of reaction mixture was adjusted to 5-6 using AcOH, and stirring continued for 3 h at room temperature. The mixture was quenched with water (100 mL) and extracted with EtOAc (2 x 200 mL). The combined organic layers were washed with water (100 mL), brine (100 mL), dried over anhydrous Na2S0 and concentrated under reduced pressure. The residue was purified by column chromatography (silica gel, 30% EtOAc/hexane) (Note: Polar spot was the trans-isomer) to provide compound D2-4 (12.0 g, 34%) as a white solid.
  • 25
  • [ 74124-79-1 ]
  • [ 870-46-2 ]
  • [ 5497-76-7 ]
  • C15H27N3O5 [ No CAS ]
  • 26
  • [ 870-46-2 ]
  • [ 17429-02-6 ]
  • tert-butyl N-[(4-hydroxy-4-methylcyclohexylidene)amino]carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.39 g In methanol; at 20℃; for 48h; To a solution of <strong>[17429-02-6]4-hydroxy-4-methyl-cyclohexanone</strong> (6.14 g, 47.88 mmol) in MeOH (60 mL) was added fe/ -butyl carbazate (6.64 g, 50.28 mmol). The reaction mixture was stirred at room temperature for 2 days. Then, the solvent was removed under reduced pressure and the obtained residue dissolved in DCM, washed with water, dried over Na2S04 and concentrated under reduced pressure. Further purification by flash column chromatography on silica gel eluting with 0-100% EtOAc in heptane followed by column chromatography on silica gel eluting with 0-10% MeOH in DCM and recrystallization from ether and column chromatography on silica gel eluting with 0-100% EtOAc in DCM gave fe/ -butyl /V-[(4-hydroxy-4-methyl-cyclohexylidene)amino]carbamate (1 .39 g, 2.76 mmol, 6% yield) as a solid. UPLC-MS (ES+, Short acidic): 3.50 min, m/z 243.2 [M+H]+
  • 27
  • [ 870-46-2 ]
  • [ 2592-18-9 ]
  • C14H27N3O6 [ No CAS ]
  • 28
  • [ 15855-06-8 ]
  • [ 870-46-2 ]
  • tert-butyl 2-(2-chloro-6-methoxyisonicotinoyl)hydrazine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of <strong>[15855-06-8]2-chloro-6-methoxyisonicotinic acid</strong> (19) (188mg, 1.0mmol) in dichloromethane (10mL) was added oxalyl chloride (381mg, 3.0mmol) and 3 drops of DMF as catalyst. The mixture was stirred at room temperature for 1h and the solvent and excess oxalyl chloride was removed under vacuum. The residue was dissolved in the dichloromethane. To the solution was added tert-butyl hydrazinecarboxylate (132mg, 1.0mmol) and triethylamine (303mg, 3.0mmol) at 0C. The mixture was stirred at room temperature until the reaction was completed as determined by TLC. Then, the mixture was washed with water, saturated brine, and dried over anhydrous MgSO4. After filtration and concentration, the crude product was collected. 1H NMR (400MHz, DMSO-d6) delta 10.50 (s, 1H, -OCONH), 9.08 (s, 1H, CONH), 7.42 (s, 1H, Ar-H), 7.19 (s, 1H, Ar-H), 3.90 (s, 3H, -O-CH3), 1.43 (s, 9H, -C-CH3).
  • 29
  • [ 943541-20-6 ]
  • [ 870-46-2 ]
  • tert-butyl (2E)-2-{2-[difluoro(quinolin-6-yl)acetyl]-6-(1-methyl-1H-pyrazol-4-yl)pyridazin-3(2H)-ylidene}hydrazinecarboxylate [ No CAS ]
 

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