Acetyl chloride → N-[5-(2-Acetylamino-4-pyridyl)-4-(4-methoxyphenyl)-1,3-thiazol-2-YL]acetamide

HRID 1727359

Reaction equation

[NH2:1][C:2]1[S:3][C:4]([C:15]2[CH:20]=[CH:19][N:18]=[C:17]([NH2:21])[CH:16]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:6]=1.[C:22](Cl)(=[O:24])[CH3:23].C(=O)([O-])O.[Na+].CN(C)[C:33](=[O:35])[CH3:34]>CN(C)C1C=CN=CC=1>[C:22]([NH:21][C:17]1[CH:16]=[C:15]([C:4]2[S:3][C:2]([NH:1][C:33](=[O:35])[CH3:34])=[N:6][C:5]=2[C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[CH:20]=[CH:19][N:18]=1)(=[O:24])[CH3:23]

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of 4-[2-amino-4-(4-methoxyphenyl)-1,3-thiazol-5-yl]-2-pyridylamine (0.40 g, 1.4 mmol) and 4-dimethylaminopyridine (0.055 g, 0.45 mmol) in N,N-dimethylacetamide (10 mL) was added acetyl chloride (0.3 mL, 4.2 mmol), and the mixture was stirred for 14 hours at 70° C. An aqueous sodium hydrogen carbonate solution was poured into the reaction mixture, and extracted with ethyl acetate. The extracts were washed with brine, then, dried and concentrated. The crude crystal was recrystallized from ethanol to obtain a title compound (0.30 g, yield 58%).

Workup

extractionextracted with ethyl acetate
washThe extracts were washed with brine
customdried
concentrationconcentrated
customThe crude crystal was recrystallized from ethanol

Sources & evidence

ORD record: ord-bfd3eac912c047cb81685582468560e3
Source dataset: uspto-grants-2009_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07495018B2

Linked notes

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