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Chemical Structure| 5781-53-3 Chemical Structure| 5781-53-3

Structure of 5781-53-3

Chemical Structure| 5781-53-3

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CAS No.: 5781-53-3

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Product Details of [ 5781-53-3 ]

CAS No. :5781-53-3
Formula : C3H3ClO3
M.W : 122.51
SMILES Code : O=C(OC)C(Cl)=O
MDL No. :MFCD00000705
InChI Key :ZXUQEPZWVQIOJE-UHFFFAOYSA-N
Pubchem ID :79846

Safety of [ 5781-53-3 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H226-H314
Precautionary Statements:P280-P305+P351+P338-P310
Class:8(3)
UN#:2920
Packing Group:Ⅱ

Computational Chemistry of [ 5781-53-3 ] Show Less

Physicochemical Properties

Num. heavy atoms 7
Num. arom. heavy atoms 0
Fraction Csp3 0.33
Num. rotatable bonds 2
Num. H-bond acceptors 3.0
Num. H-bond donors 0.0
Molar Refractivity 22.82
TPSA ?

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

43.37 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.13
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

1.06
Log Po/w (WLOGP)?

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

-0.08
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.

-0.5
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

0.38
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

0.4

Water Solubility

Log S (ESOL):?

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

-1.14
Solubility 8.97 mg/ml ; 0.0732 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.

-1.56
Solubility 3.36 mg/ml ; 0.0274 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

-0.47
Solubility 41.0 mg/ml ; 0.335 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.

-6.29 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

 2.0
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)

 1.65

Application In Synthesis of [ 5781-53-3 ]

* 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 [ 5781-53-3 ]

[ 5781-53-3 ] Synthesis Path-Downstream   1~17

  • 1
  • [ 5781-53-3 ]
  • [ 1591-38-4 ]
  • [ 54166-71-1 ]
YieldReaction ConditionsOperation in experiment
EXAMPLE 40 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 3, giving 4.24 g of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.38; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 23 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 12, giving 4.24 g. of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.28; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 23 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 12, giving 4.24 g. of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.28; H, 4.80; N, 11.11: Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 23 2'-Carbamyl-3'-methoxyoxanilic acid methyl ester. 96. 6-Amino-o-anisamide (4.98 g., 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 12, giving 4.24 g. of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.28; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 40 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 3, giving 4.24 g of the title compound, m.p. 195-198 C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.38; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.
EXAMPLE 40 2'-Carbamoyl-3'-methoxyoxanilic acid methyl ester. 96 6-Amino-o-anisamide (4.98 g, 0.03 mole) is condensed with 3.04 ml. (0.033 mole) of methyl oxalyl chloride in a manner similar to example 3, giving 4.24 g of the title compound, m.p. 195-198C., after crystallization from methanol. Elemental Analysis for C11 H12 N2 O5: Calc'd: C, 52.38; H, 4.80; N, 11.11. Found: C, 52.30; H, 4.94; H, 11.40.

  • 2
  • [ 5781-53-3 ]
  • [ 39796-52-6 ]
  • [ 96042-88-5 ]
  • 3
  • [ 5781-53-3 ]
  • [ 120-72-9 ]
  • [ 18372-22-0 ]
  • 4
  • [ 5781-53-3 ]
  • [ 6628-86-0 ]
  • [ 53308-95-5 ]
  • 2-(7-chloro-2,3-dioxo-1,2,3,5-tetrahydro-benzo[<i>e</i>][1,4]diazepin-4-yl)-pentanoic acid amide [ No CAS ]
  • 5
  • [ 5781-53-3 ]
  • [ 53308-95-5 ]
  • [ 552-89-6 ]
  • 2-(2,3-dioxo-1,2,3,5-tetrahydro-benzo[<i>e</i>][1,4]diazepin-4-yl)-pentanoic acid amide [ No CAS ]
  • 6
  • [ 5781-53-3 ]
  • [ 271-34-1 ]
  • [ 357263-50-4 ]
YieldReaction ConditionsOperation in experiment
70% Acylation of azaindole, method B: Preparation of Methyl(5-azaindol-3-yl)-oxoacetate 2b: 5-Azaindole (1b) (0.5 g, 4.2 mmol) was added to a suspension of AlCl3 (2.8 g, 21.0 mmol) in CH2Cl2 (100 ml). Stirring was continued at room temperature for 1 hour before methyl chlorooxoacetate (2.5 g, 21.0 mmol) was added dropwise. The reaction was stirred for 8 hours. After 20 ml of MeOH was added cautiously to quench the reaction, solvents were removed under vacuum. The solid residue was purified by silica gel column chromatography (EtOAc/MeOH=10:1) to afford 0.6 g (70%) of the acylated product 2b. Characterization of compounds 2: Compound 2b (Methyl(5-azaindol-3-yl)-oxoacetate): 1H NMR (500 MHz, CD3OD) δ 9.61 (s, 1H), 9.02 (s, 1H), 8.59 (d, 1H, J=6.63 Hz), 8.15 (d, 1H, J=6.60 Hz), 4.00 (s, 3H); 13C NMR (125 MHz, CD3OD) δ 178.9, 163.0, 145.6, 144.2, 138.3, 135.0, 124.7, 116.3, 112.1, 53.8. MS m/z: (M+H)+ calcd for C10H9N2O3: 205.06; found 205.04. HPLC retention time: 0.32 minutes (column A).
AlCl3; In dichloromethane; Preparation of Methyl (5-azaindol-3-yl)-oxoacetate 2b: 5-Azaindole 1b (0.5 g, 4.2 mmol) was added to a suspension of AlCl3 (2.8 g, 21.0 mmol) in CH2Cl2 (100 ml). Stirring was continued at room temperature for 1 hour before methyl chlorooxoacetate (2.5 g, 21.0 mmol) was added dropwise.
  • 7
  • [ 5781-53-3 ]
  • [ 28992-50-9 ]
  • resin-bound isobutylamine [ No CAS ]
  • (3-isobutylamino-[1,2,4]oxadiazol-5-yl)-oxo-acetic acid methyl ester [ No CAS ]
  • 8
  • [ 5781-53-3 ]
  • [ 619331-35-0 ]
  • [ 954215-11-3 ]
YieldReaction ConditionsOperation in experiment
99% E2 Methyl 2-(7-bromo-4-methoxy-6-azaindol-3-yl)-2-oxoacetate To a solution of AlCl3 (0.587 g, 4.40 mmol) in DCM-MeNO2 (4:1, 3 mL) was added a solution of <strong>[619331-35-0]7-bromo-4-methoxy-6-azaindole</strong> (0.100 g, 0.440 mmol) in DCM-MeNO2 (4:1, 1 mL), followed by methyl oxalyl chloride (0.162 mL, 1.76 mmol). The resulting deep orange solution was stirred at room temperature for 1 h and then it was quenched by the slow addition of 1M NH4OH. The mixture was extracted with ethyl acetate (2*) and the combined organic phases were dried (MgSO4) and evaporated to give the title compound (0.136 g, 99%) as a white solid weighing: 1H-NMR (400 MHz, DMSO-d6) δ 13.16 (s, 1H), 8.41 (d, J=3.0 Hz, 1H), 7.84 (s, 1H), 3.92 (s, 3H), 3.86 (s, 3H).
Process for the Preparation of Compound J-In-3 from J-In-2:[00149] To a stirred solution of aluminum chloride (4 eq.) in dry dichloromethane under nitrogen atmosphere was added J-In-2 (1 eq.) portion wise and the reaction mixture was stirred at room temperature for 2h. In a separate flask, to a stirred solution of aluminum chloride (6 eq.) in dry dichloromethane under nitrogen atmosphere was added methoxy oxalylchloride (3 eq.) drop wise. The reaction mixture was allowed to stir at room temperature for 2hrs. Then this reaction mixture was added slowly to the above reaction mixture for about 30min and stirred for 16h at room temperature. The reaction mixture was quenched with saturated ammonium acetate solution to pH-7. The resulting mixture was extracted with ethyl acetate. The combined organic layer was washed with brine, dried over sodium sulfate, filtered and concentrated. The crude product was purified by column chromatography using 60-120 silica gel and 25% ethyl acetate in hexane as eluent to afford J-In-3.
  • 9
  • [ 5781-53-3 ]
  • [ 5271-27-2 ]
  • [ 960403-76-3 ]
YieldReaction ConditionsOperation in experiment
76% With triethylamine; In dichloromethane;Cooling; -Methyl-3-phenylpiperazine (17.6 g; 0.1 mol) was dissolved in 100 dichloromethane.Triethylamine (5 ml; ca 0.03 mol) was added. A solution of methyl chlorooxalate (10 ml; 0.10 mol) in dichloromethane was slowly added under cooling. After the total addition a white suspension was formed. TLC showed complete conversion. The mixture was quenched with 10percent sodium carbonate. The organic layer was washed again with carbonate, dried and evaporated to an oil (25.5 g; 97 percent).TLC: quite pure, some minor polar impurities. GC: chiral separation possible15.7/16.0 min (contains ca. 0.4percent of 3.8 min impurity (present in starting piperazine) that can be used as internal standard).The material solidifies on standing. Attempt to recrystallise from CH2CI2/hexane. This gives 20 g of light-brown solid (76 percent). mp 103-5°C.GC: 3.8 min impurity is removed.
  • 10
  • [ 5781-53-3 ]
  • TFA salt of amine [ No CAS ]
  • [ 21461-84-7 ]
  • [ 118994-86-8 ]
  • [ 321434-76-8 ]
YieldReaction ConditionsOperation in experiment
With 1-hydroxy-7-aza-benzotriazole; Ph3SnH; azobisisobutyronitrile; ammonium chloride; 4-pyrrolidin-1-ylpyridine; N-ethyl-N,N-diisopropylamine; lithium hexamethyldisilazane; In tetrahydrofuran; triethanolamine; hexane; 4-(dicyanomethylene)-2-methyl-6-(p-dimethylaminostyryl)-4H-pyran; ethyl acetate; toluene; EXAMPLE 24 (4R)-N-[(2-chloro-6-methylphenyl)methyl]-3-[(2S,4S)-5-[((3S,4S)-3,4-dihydro-3-hydroxy-2H-1-benzopyran-4-yl)amino]-2-hydroxy-4-(5-oxazolylmethyl)-1,5-dioxopentyl]-5,5-dimethyl-4-thiazolidinecarboxamide (S)-(+)-5-oxo-2-tetrahydrofurancarboxylic acid (290 mg; 2.2 mmol) was suspended in anhydrous DCM (10 mL) and the TFA salt of amine from Example 23 Step C (769 mg; 1.86 mmol) was added; dissolution occurred. The solution was cooled to 0 C., and DIEA (1.3 mL; 7.44 mmol) added followed by HOAt (229 mg; 2.2 mmol) and then PyBop (1.14 g; 2.2 mmol). The next morning, the reaction mixture was poured into ethyl acetate and washed with water and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo followed by flash column chromatography (75% EtOAc/hexane) provided the desired compound. To a solution of the intermediate obtained in Step A above (150 mg; 0.37 mmol) in 2.5 mL anhydrous THF at -78 C. under nitrogen was added dropwise LHMDS (0.77 mmol; 0.77 mL). After 1 hr 20 min, a solution of <strong>[118994-86-8]5-oxazolecarboxaldehyde</strong> (39 mg; 0.40 mmol) in 0.5 mL anhydrous THF was added dropwise. After 1.25 hr, the reaction was quenched with saturated ammonium chloride. The mixture was poured into EtOAc and washed with 50% brine and brine. Drying (MgSO4), filtration, and removal of the solvent in vacuo followed by flash column chromatography (gradient elution 75% EtOAc/hexane to 100% EtOAc) provided the desired compound. To a solution of the material from Step B (67 mg; 0.13 mmol) in 0.75 mL anhydrous THF cooled to 0 C. was added TEA (20 muL; 0.143 mmol) and 4-pyrrolidinopyridine (cat.); methyl oxalyl chloride (13 muL; 0.143 mmol) was then added dropwise. After 2.25 hours, the reaction mixture was diluted with EtOAc (40 mL) and washed with NaHCO3 solution and brine. Drying (MgSO4), filtration, and removal of the solvent in vacuo followed by flash column chromatography (75% EtOAc/hexane) provided the desired compound. To a solution of the intermediate from Step C (50 mg; 0.084 mmol) in anhydrous toluene (1.0 mL) was added AIBN (cat.) followed by Ph3SnH (43 muL; 0.168 mmol). Twenty minutes at reflux was followed by 1.5 hours at 100 C. Removal of solvent in vacuo was followed by flash column chromatography (75% EtOAc/hexane) to provide the desired compound.
  • 11
  • [ 5781-53-3 ]
  • [ 122-72-5 ]
  • [ 951160-37-5 ]
YieldReaction ConditionsOperation in experiment
With aluminum (III) chloride; In dichloromethane; at 0 - 20℃; A solution of 5 g 3-phenyl propylacetate and 4.1 g methyl oxalyl chloride in 20 mL DCM was added slowly to a mixture of 8.2 g anhydrous aluminum chloride in 30 mL DCM at 00C. The reaction mixture is then allowed to warm up to room temperature overnight. Aqueous work-up with saturated NHjCl and EtOAc followed by SGC using 3:1 hexanes and EtOAc afforded the title compound as clear oil. 1HNMR (CDCl3, 500 MHz) delta: 7.97 (d, 8.2 Hz, 2H)5 7.35 (d, 8.2 Hz, 2H), 4.11 (t, 6.3 Hz, 2H), 3.99 (s, 3H),2.80 (t, 7.7 Hz, 2H), 2.07 (s, 3H), 1.98-2.03 (m, 2H).
  • 12
  • [ 5781-53-3 ]
  • [ 518048-03-8 ]
  • [ 518048-04-9 ]
  • 13
  • [ 5781-53-3 ]
  • [ 52023-68-4 ]
  • [ 892491-36-0 ]
  • 14
  • [ 5781-53-3 ]
  • [ 6971-44-4 ]
  • [ 1416267-46-3 ]
YieldReaction ConditionsOperation in experiment
With pyridine; In dichloromethane; at 50℃; for 2h; Step A: A solution of methyl chlorooxoacetate (2.01 g, 16.37 mmol), N-methyl- N-(4-pyridinylmethyl)amine (2.0 g, 16.37 mmol) and pyridine (1.6 mL, 19.64 mmol) in anhydrous dichloromethane (10 mL) was stirred at 50 C for 2 h. The mixture was evaporated in vacuo and the residue was purified by flash column chromatography on silica gel (40% - 100% EtOAc in hexanes) to afford methyl 2-(methyl(pyridin-4- ylmethyl)amino)-2-oxoacetate (77) as a pale yellow oil (0.96 g).
  • 15
  • [ 5781-53-3 ]
  • [ 120068-37-3 ]
  • N,N'-bis[3-cyano-4-trifluoromethylsulfinyl-1-(2,6-dichloro-4-trifluoromethylphenyl)pyrazolyl]ethanediamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
81.7% With sodium carbonate; In 1,4-dioxane; at 110℃; for 12h; In 100 mLReactorAfter addition of 30 mL dioxane,9g1- (2,6-dichloro-4-trifluoromethyl) phenyl-3-cyano-4-trifluoromethylsulfinyl-5-aminopyrazole,2.65 g of sodium carbonate,1.23 g of methyl oxalyl chloride,After mixing,Put the reactor into the oven,The reaction temperature was 110 ,The reaction time was 720 minutes.After completion of the reaction,The solvent was removed by rotary evaporation,Adjust the pH to neutral,extraction,After drying over anhydrous magnesium sulfate,A light yellow solid was obtained by column chromatography over petroleum ether and ethyl acetate (4: 1)7.58g () 2,The yield was 81.7%
  • 16
  • [ 5781-53-3 ]
  • methyl 2-{3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl}ethanimidate [ No CAS ]
  • [ 51169-05-2 ]
  • methyl 3-({3-(4-chlorophenyl)-5-oxo-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-4,5-dihydro-1H-1,2,4-triazol-1-yl} methyl)-1-(pyridin-2-yl)-1H-1,2,4-triazole-5-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% A solution of methyl 2- {3 -(4-chlorophenyl)-5-oxo-4- [(2S)-3 ,3 ,3 -trifluoro-2-hydroxypropyl] -4,5- dihydro-1H-1,2,4-triazol-1-yl}ethanimidate (Example 7A; 1.00 g, 2.64 mmol) in tetrahydrofuran (20 ml) was cooled to 0C and treated with methyl chloro(oxo)acetate (270 jil, 2.9 mmol). The resulting mixture was stirred for 30 mi 2-Hydrazinylpyridine hydrochloride (1:1) (423 mg, 2.90 mmol) and N,N-diisopropylethylamine (1.0 ml, 5.8 mmol) were added, the reaction mixture waswarmed up to room temperature and stirred for 30 mm, followed by 1 h at 120C in a sealed vial under microwave irradiation. The crude product was purified by preparative HPLC (Method 5). Lyophilisation of the product containing fractions afforded 483 mg (33% of th.) of the title compound.LC-MS (Method 3): R = 1.79 mm; MS (ESIpos): mlz = 524 [M+H]1H-NMR (400 MHz, DMSO-d6) [ppm]: 3.820 (0.78), 3.844 (1.02), 3.858 (16.00), 3.880 (1.25),3.990 (1.15), 3.998 (1.28), 4.026 (0.81), 4.035 (0.78), 5.187 (7.66), 6.905 (2.15), 6.921 (2.27),7.564 (1.07), 7.577 (1.17), 7.583 (1.19), 7.595 (1.26), 7.608 (3.70), 7.613 (1.40), 7.625 (1.82),7.629 (4.90), 7.743 (0.97), 7.750 (5.02), 7.755 (1.55), 7.766 (1.45), 7.771 (3.70), 7.815 (1.92),7.835 (2.21), 8.099 (0.94), 8.103 (0.94), 8.118 (1.49), 8.122 (1.54), 8.138 (0.77), 8.142 (0.75),8.527 (1.25), 8.532 (1.40), 8.539 (1.33), 8.544 (1.33).
  • 17
  • [ 5781-53-3 ]
  • [ 98-55-5 ]
  • rac-methyl (2-(4-methylcyclohex-3-en-1-yl)propan-2-yl) oxalate [ No CAS ]
 

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