Pyridine → HCID 10209850, compound

HRID 1168340Notes

Reaction equation

HRID 1168340 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([N:8]([CH3:28])[C:9](=[O:27])[C:10]([C:13]2[CH:18]=[C:17]([C:19]([F:22])([F:21])[F:20])[CH:16]=[C:15]([C:23]([F:26])([F:25])[F:24])[CH:14]=2)([CH3:12])[CH3:11])=[C:4]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH:3]=1.N1C=CC=CC=1.[CH:42]1([C:45](Cl)=[O:46])[CH2:44][CH2:43]1>ClCCl>[F:22][C:19]([F:20])([F:21])[C:17]1[CH:18]=[C:13]([C:10]([CH3:12])([CH3:11])[C:9]([N:8]([CH3:28])[C:5]2[C:4]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=3[CH3:35])=[CH:3][C:2]([NH:1][C:45]([CH:42]3[CH2:44][CH2:43]3)=[O:46])=[N:7][CH:6]=2)=[O:27])[CH:14]=[C:15]([C:23]([F:26])([F:24])[F:25])[CH:16]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 77637Cyclopropanecarbonyl chlorideHCID 9913704HCID 9913704, compound

Product 1

HCID 10209850HCID 10209850, compoundYield 54.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 100 mg (0.20 mmol) N-(6-amino-4-o-tolyl-pyridin-3-yl)-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide in 3 ml dichloromethane were added 2 ml pyridine and 23 mg (0.22 mmol) cyclopropanecarboxylic acid chloride at 0° C. After stirring for 2 days at room temperature, the solvent was removed in vacuo and the residue was purified by flash-chromatography to give 61 mg (54%) of the title compound as white solid. MS m/e (%): 586 (M+Na+, 25), 564 (M+H+, 100).

Workup

  1. customthe solvent was removed in vacuo
  2. customthe residue was purified by flash-chromatography

Sources & evidence

ORD record
ord-38601fb48a9946ba8d2adb84f9810f16
Source dataset
uspto-grants-2003_09
Patent number
US06624176B2

Reaction notes

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