Pyridine → HCID 178433640, compound

HRID 2271111Notes

Reaction equation

HRID 2271111 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([C:8]2[C:9]3[C:10]([C:15](=[O:25])[N:16]([C:18]4[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][CH:19]=4)[N:17]=3)=[CH:11][NH:12][C:13]=2[CH3:14])[CH:5]=[CH:6][CH:7]=1.N1C=CC=CC=1.[CH3:32][S:33](Cl)(=[O:35])=[O:34]>C(O)CO.COC>[Cl:24][C:21]1[CH:22]=[CH:23][C:18]([N:16]2[C:15](=[O:25])[C:10]3=[CH:11][NH:12][C:13]([CH3:14])=[C:8]([C:4]4[CH:3]=[C:2]([NH:1][S:33]([CH3:32])(=[O:35])=[O:34])[CH:7]=[CH:6][CH:5]=4)[C:9]3=[N:17]2)=[CH:19][CH:20]=1

Participants

6

Reactant 3

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 178433638HCID 178433638, compound

Product 1

HCID 178433640HCID 178433640, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 174Ethylene GlycolSolventHCID 8254Dimethyl EtherSolvent

Procedure

To a stirred solution of 7-(3-aminophenyl)-2-(4-chlorophenyl)-2,5-dihydro-6-methylpyrazolo[4,3-c]pyridin-3-one (0.100 g, 0.285 mmol) in anhydrous ethylene glycol, dimethyl ether (5 ml) was added portionwise, over a few hours, pyridine (0.228 ml, 2.82 mmol) and methanesulphonyl chloride (0.174 ml, 2.25 mmol), and the mixture was heated at 50° C. for 1.5 h. The solvent was removed in vacuo and the residue was purified by flash chromatography (silica gel, 5-10% MeOH/CH2Cl2) to leave 0.1119 g (92%) of the title compound as a yellow solid; mp 332-341° C. (CH2Cl2-MeOH-EtOAc); 1H NMR (360 MHz, DMSO-d6) δ2.28 (3H, s), 3.06 (3H, s), 7.24 (2H, dd, J 7.9, J′1.8 Hz), 7.40 (1H, m), 7.43 (2H, d, J 9.0 Hz), 7.46 (1H, t, J 8.0 Hz), 8.13 (2H, d, J 9.0 Hz), 8.56 (1H, s); MS (ES+) m/z 429/431[MH]+. Anal. found: C, 55.89; H, 4.06; N, 12.60. C20H17CLN4O3S.0.2H2O requires: C, 55.54; H, 4.06; N, 12.95%.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by flash chromatography (silica gel, 5-10% MeOH/CH2Cl2)

Sources & evidence

ORD record
ord-d037af4d06c2435992bea246e52f998c
Source dataset
uspto-grants-2001_12
Patent number
US06333336B1

Reaction notes

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