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Chemical Structure| 23100-12-1 Chemical Structure| 23100-12-1

Structure of 23100-12-1

Chemical Structure| 23100-12-1

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CAS No.: 23100-12-1

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Product Details of [ 23100-12-1 ]

CAS No. :23100-12-1
Formula : C6H4ClNO
M.W : 141.56
SMILES Code : C1=NC(=CC=C1C=O)Cl
MDL No. :MFCD03095223
Boiling Point : No data available
InChI Key :AFWWKZCPPRPDQK-UHFFFAOYSA-N
Pubchem ID :2764053

Safety of [ 23100-12-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319-H335
Precautionary Statements:P261-P305+P351+P338

Computational Chemistry of [ 23100-12-1 ] Show Less

Physicochemical Properties

Num. heavy atoms 9
Num. arom. heavy atoms 6
Fraction Csp3 0.0
Num. rotatable bonds 1
Num. H-bond acceptors 2.0
Num. H-bond donors 0.0
Molar Refractivity 34.63
TPSA ?

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

29.96 ?2

Lipophilicity

Log Po/w (iLOGP)?

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

1.26
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

1.23
Log Po/w (WLOGP)?

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

1.55
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.

0.4
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

2.16
Consensus Log Po/w?

Consensus Log Po/w: Average of all five predictions

1.32

Water Solubility

Log S (ESOL):?

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

-1.92
Solubility 1.7 mg/ml ; 0.012 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.

-1.46
Solubility 4.95 mg/ml ; 0.0349 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

-2.56
Solubility 0.387 mg/ml ; 0.00274 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

 Yes
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

 Yes
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

 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)

 1.28

Application In Synthesis of [ 23100-12-1 ]

* 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 [ 23100-12-1 ]

[ 23100-12-1 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 21543-49-7 ]
  • [ 23100-12-1 ]
YieldReaction ConditionsOperation in experiment
96% With oxalyl dichloride; triethylamine; In dimethyl sulfoxide; at -78 - 20℃; for 2.5h; According to a procedure of Lee et al. [22] oxalylchloride (3.81 g, 30.0 mmol, 3.0 eq) was dissolved in CH2Cl2 (35 mL) at -78C (dry ice/acetone). Then DMSO (46.9 g, 0.60 mol, 60.0 eq.)was added dropwise under stirring and the reaction mixture was stirred for additional 30 min at -78C. Then 2-chloro-5-(hydroxymethyl)pyridine (1.44 g, 10.0 mmol, 1.00 eq) was dissolved in CH2Cl2(10 mL) and added dropwise with a syringe to the cold reaction mixture. Afterwards, the reaction mixture was stirred for 40 min at -78C and NEt3 (91.9 g, 0.90 mol, 90.0 eq) was added to the reaction mixture at a rate of 2.0 mL/min. The reaction mixture was stirred for 1 h at -78C, followed by another 1.5 h stirring at r.t. The reaction mixture was then diluted with Et2O (60 mL) and the organic phase was washed successively withNaHCO3(sat., aq., 2 × 30 mL), KHSO4(1 M, aq., 60 mL) and NaHCO3(sat., aq., 30 mL). After phase separation the organic phase was dried over Na2SO4, the solid removed by filtration and the solvent was removed in vacuum. Further cleaning with liquid chromatography(LC) (SiO2, n-pentane/EtOAc/NEt3= 200/100/6) gave the desired product as yellowish solid (1.35 g, 96%).
94% With Br3(1-)*C10H15NPol(1+); dimethyl sulfoxide; at 20℃; for 6h; General procedure: To a mixture of alcohol in dry DMSO (10 volume) was added 1 equiv of polymer bromide and the reaction mixture was stirred at room temperature for a given period of time (Table 1). After the completion of the reaction, the reaction mixture was filtered and the polymer bed washed with DMSO. Combined DMSO layers were quenched with ice-water mixture and extracted with ether. The ether layer was given water wash, brine wash, dried over anhydrous sodium sulphate, and concentrated to get the pure carbonyl compounds. All the products were characterized by NMR and MS analysis.
87% With manganese(IV) oxide; In chloroform; at 60℃; To a solution of the alcohol from above (481 mg, 3.35 mmol) in CHCl3 (25 mL) was added MnO2 (85%, 3.14 g, 30.7 mmol) and the suspension stirred at 60 0C overnight. The reaction was cooled, filtered through Celite, washing the cake with CH2Cl2 and MeOH and the resultant filtrate concentrated to afford the desired aldehyde (0.41 g, 87%) as a yellow solid. To a solution of 6-chloro-3-pyridinecarboxaldehyde (210 mg, 1.48 mmol) and ρyrimidine-5-boronic acid (207 mg, 1.67 mmol) in THF/DME/2 M Na2CO3 (1:2:1, 4 mL) was added Pd(PPh3)4 (154 mg, 0.13 mmol) and the reaction stirred under argon at 90 0C overnight. Standard work-up and purification by column chromatography on silica gel (CH2Cl2ZMeOH, 95:5) afforded -pyrimidm-S-yl-pyridme-S-carbaldehyde (80 mg, 29%) as a yellow solid. 1H NMR (CDCl3) δ 7.96 (d, IH, J= 8.1 Hz), 8.32 (dd, IH, J= 8.1, 1.5 Hz), 9.20 (d, IH, J = 1.5 Hz), 9.32 (s, IH), 9.42 (s, 2H), 10.18 (s, IH).
89%Chromat. With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; In dichloromethane; at 25℃; for 0.5h; General procedure: DBDMH (1 mmol) was added to a mixture of 1b (1 mmol) and dichloromethane (20ml). The reaction was kept at room temperature. After the mixture was stirred for0.5h, the mixture was washed with water (330 ml),dried with anhydrous MgSO4,filtered, and vacuum evaporated. The residue was purified by column chromatography (silica gel: petroleum ether/ethyl acetate, 30:1) to afford the product as light yellowsolid (93% yield).
15 g With pyridinium chlorochromate; In dichloromethane; at 0 - 20℃; for 2h; To a solution of PCC (58 g, 0.27 mol) in DCM (1500 ml) was added the product of the proceeding step (26 g, 0.184mol) as a solution in DCM drop wise at 0C. The mixture was then stirred for 2h at 20C. It was filtered through diatomaceous earth and the filter contents were washed with DCM. The organic phase was concentrated to give the crude product, which was purified by column chromatography to give the product (15 g, yield: 60.1 %). 1H NMR (400 MHz, CDCI3): δ 10.067 (s, 1 H), 8.874 (s, 1 H, J=3Hz), 8.158-8.138 (d, 1 H, J=8Hz), 7.534-7.513 (d, 1 H, J=8Hz)
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; water-d2; alpha cyclodextrin; at 60℃; for 3h;Green chemistry; General procedure: To a clean and dry small vial, a solution of substrate 1 (15.0 μmol, 1.0 equivalent) was added using an aqueous cyclodextrin solution (1.0 mL) of the specified concentration in D2O. DBDMH 3 (4.3 mg, 15.0 μmol, 1.0 equivalent) was added to the reaction mixture and sonicated to make sure that the reagents were well suspended. The reaction mixture was heated at 60 C with occasional shaking to maintain the homogeneity of the solution. After the desired period of time, the 1H NMR spectrum of the reaction mixture was recorded to determine the percent conversion.

  • 2
  • [ 23100-12-1 ]
  • [ 124755-24-4 ]
  • [ 201293-11-0 ]
  • 3
  • [ 25999-04-6 ]
  • [ 23100-12-1 ]
  • N-(5-formylpyridin-2-yl)morpholine-4-sulfonamide [ No CAS ]
  • 4
  • [ 23100-12-1 ]
  • [ 108-95-2 ]
  • [ 173282-69-4 ]
YieldReaction ConditionsOperation in experiment
99% With caesium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; at 100℃; for 10h; To a stirred solution of 6-chloronicotinaldehyde (2.0 g, 14.1 mmol, 1.0 eq.) and phenol (1.32 g, 14.1 mmol, 1.0 eq.) in DMF (20 mL) was added Cs2CO3 (5.5 g, 16.9 mmol, 1.2 eq.) and CuCl (1.61 g, 16.9 mmol, 1.2 eq.). The resulting mixture heated at 100 C. for 10 h. Following this, reaction was allowed to cool to RT and filtered through celite pad, the celite pad washed with ethyl acetate and water. The aqueous layer was separated extracted using ethyl acetate (3×30 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous Na2SO4, filtered and concentrated under vacuum to get the solid residue. The crude was purified by normal phase silica-gel column provided title compound (2.8 g, 99%). LCMS: 200.0 [M+1]+; 1H NMR (400 MHz, DMSO-d6) δ ppm 9.99 (s, 1H) 8.70 (d, J=2.19 Hz, 1H) 8.27 (dd, J=8.55, 2.41 Hz, 1H) 7.43-7.52 (m, 2H) 7.18-7.32 (m, 4H)
92% With caesium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; for 10h;Reflux; To a solution of 6-chloronicotinaldehyde (3) (0.28 g, 2 mmol) and phenol (0.19 g, 2 mmol) in DMF (30 mL) was added Cs2CO3 (0.78 g, 2.4 mmol) and CuCl (0.24 g, 2.4 mmol), then the mixture was refluxed for 10 h and then cooled to room temperature. The mixture was extracted with EtOAc, and the extract was washed successively with water and brine, and dried over anhydrous Na2SO4. The crude product was purified by recrystallization using methanol to give compound 4 as a white solid (0.36 g, 92%); mp = 91-93 C; 1H NMR (400 MHz, CDCl3): δ 9.98 (s, 1H, CHO), 8.63 (s, 1H, Py-H), 8.19 (d, J = 8.4 Hz, 1H, Py-H), 7.46 (t, J = 7.6 Hz, 2H, Ar-H), 7.30 (d, J = 7.6 Hz, 1H, Ar-H), 7.17 (d, J = 7.6 Hz, 2H, Ar-H), 7.16 (d, J = 8.4 Hz, 1H, Py-H); 13C NMR (100 MHz, CDCl3) δ 189.4, 167.3, 153.0, 152.8, 138.7, 129.9, 127.7, 125.8, 121.6, 112.1. ESI-HRMS (m/z): Calcd for C12H10NO2 [M+H]+ 200.0706. Found 200.0708.
92% With caesium carbonate; copper(l) chloride; In N,N-dimethyl-formamide; for 10h;Reflux; 6-chloropyridine-3-carbaldehyde (2) (0.28 g, 2 mmol),Phenol (0.I9 g, 2 mmol) was dissolved in DMF (30 mL).Then Cs2CO3 (0.78 g, 2.4 mmol) and CuCl (0.24 g, 2.4 mmol) were added.It was then heated to reflux for 10 hours. Add ethyl acetate and water,Wash the organic phase with saturated brine, dry over anhydrous sodium sulfate, and dissolve.Recrystallization from methanol gave 0.36 g of a white solid.Yield 92%.
1.38 g With potassium carbonate; In N,N-dimethyl-formamide; at 110℃; for 0.5h;Microwave irradiation; 6-Chloro-pyridine-3-carbaldehyde (1.50 g; 10.6 mmol) and Phenol (1.20 g; 12.7 mmol) were dissolved in DMF (10 ml) in a microwave vial; K2CO3 (2.20 g; 15.9 mmol) was added and the reaction mixture was stirred at 110 C. during 30 minutes. The reaction mixture was diluted with water (50 ml) and the obtained precipitate was filtered off, washed with water and dried in the air. Obtained 1.38 g of the desired compound. (0290) Example 5p: HPLC-MS (Method): Z017_S04 Rt [min]: 0.93 MS: 200 [M+H]+

  • 5
  • [ 23100-12-1 ]
  • [ 2612-28-4 ]
  • C25H20F7NO3 [ No CAS ]
  • 6
  • [ 23100-12-1 ]
  • [ 2612-28-4 ]
  • C12H16ClNO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With toluene-4-sulfonic acid; In toluene; for 3h;Reflux; Add 100 mL of toluene to 13.1 g (111 mmol) of the diol (4), 17.5 g (90%; 111 mmol) of the aldehyde (3) and 1 g of p-toluenesulfonic acid, Heat for 3 hours. Then cooled, the batch is passed through silica gel (toluene). The product obtained is used in the next step without further purification.
  • 7
  • [ 23100-12-1 ]
  • [ 101990-45-8 ]
YieldReaction ConditionsOperation in experiment
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione; sulfuric acid; In dichloromethane; at 80 - 85℃; for 20h; 30 g of 2-chloro-5-aldehyde pyridine and 100 g of dichloromethane were taken and added to a reaction flask, and 100 g of 98% sulfuric acid was added. RiseWarm to 80 ~ 85 C,Dibromohydantoin 80g was added in batches.Reaction for 20 hours.Sampling was adjusted to pH=6-8 with 10% NaOH solution, and the organic phase was subjected to GC detection.2-bromo-5-bromomethylpyridineThe content is only 5.82%, the rest are raw materials and by-products.
  • 8
  • [ 23100-12-1 ]
  • [ 5326-23-8 ]
  • [ 21543-49-7 ]
YieldReaction ConditionsOperation in experiment
43.6%; 41.3% With lithium hydroxide; In ethanol; water; at 21 - 32℃; for 0.00555556h;Sonication; To a mixture of 6-chloro-pyridine-3-carbaldehyde (0.46 g, 3.2 mmol), and lithium hydroxide (0.08 g, 3.2 mmol), in a 10 mL of a solution of ethanol in water (1/1), at room temperature, was applied an ultrasonic agitation for 20 seconds (amplitude = 0.3; ti = 21C, tf = 32C; E = 709 J). The solvents were evaporated under reduced pressure and the resulting mixture was solved in CH2Cl2 and washed with water. The organic layer was collected and dried under reduced pressure to obtain 6 (0.19 g, 1.3 mmol, 41.3% yield) as a yellow oil that crystalizes within 10 minutes to become a yellow solid, with the same physicochemical properties as in the literature.11 The aqueous layer was evaporated under reduced pressure to obtain a white powder containing 6 (20%) and 7. The powder was washed with EtOAc and filtered to provide 7 (0.22 g, 1.4 mmol, 43.6% yield) as a white powder, with the same physicochemical properties as in the literature.12 6: mp 46-49 C (CH2Cl2); Rf (CH2Cl2:MeOH = 99:1) = 0.6; 1H NMR (CDCl3, 400 MHz) δ ppm 1.80 (t, J = 5.7 Hz, 1H, CH2OH), 4.74 (d, J = 5.7 Hz, 2H, CH2OH), 7.34 (d, J = 8.0 Hz, 1H, ArH), 7.70 (dd, J = 8.0, 2.4 Hz, 1H, ArH), 8.38 (d, J = 2.4 Hz, 1H, ArH); 13C NMR (CDCl3, 100 MHz) δ ppm 61.7 (CH2), 124.2 (CH), 135.3 (C), 137.8 (CH), 148.1 (CH), 150.4 (C); IR ν (cm-1): 3290, 1569, 1453, 1101, 819.
 

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