2-Chloro-N-(pyridin-2-yl)acetamide--hydrogen chloride (1/1) → HCID 67345739, compound

HRID 1910851Notes

Reaction equation

HRID 1910851 reaction equation
Cl.Cl[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=1)=O.[CH3:13][O:14][C:15]1[CH:33]=[CH:32][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25](=[S:27])[NH2:26])[C:22]([C:28]([F:31])([F:30])[F:29])=[N:21]2)=[CH:17][CH:16]=1>C(Cl)Cl>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25]3[S:27][CH:3]=[C:4]([NH:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][N:8]=4)[N:26]=3)[C:22]([C:28]([F:31])([F:29])[F:30])=[N:21]2)=[CH:32][CH:33]=1

Participants

4

Reactant 2

HCID 242014012-Chloro-N-(pyridin-2-yl)acetamide--hydrogen chloride (1/1)HCID 86674817HCID 86674817, compound

Product 1

HCID 67345739HCID 67345739, compoundYield 45.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

According to Scheme 3 Step 1: A solution of 2-chloro-N-(pyridin-2-yl)acetamide hydrochloride (0.48 mmol, 99 mg), 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole-4-carbothioamide (0.48 mmol, 150 mg) in DCM (2.5 mL) was stirred under reflux for 5 days. The crude mixture was evaporated to dryness and was purified by flash chromatography over silica gel using DCM/EtOH/NH3 (100:0:0 to 97:2.7:0.3) as eluent to yield 2-(1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazol-4-yl)-N-(pyridin-2-yl)thiazol-4-amine (0.22 mmol, 94 mg, 35%).

Workup

  1. temperatureunder reflux for 5 days
  2. customThe crude mixture was evaporated to dryness
  3. customwas purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-a17a22b8275c460794453e6acfba4561
Source dataset
uspto-grants-2013_12
Patent number
US08604033B2

Reaction notes

Loading…