Acetyl chloride → N-(2-acetyl-3,5-dimethoxy-phenyl)-4-isopropylthiazole-2-carboxamide

HRID 388665

Reaction equation

[Al](Cl)(CC)CC.[C:7](Cl)(=[O:9])[CH3:8].[CH3:11][O:12][C:13]1[CH:14]=[C:15]([NH:21][C:22]([C:24]2[S:25][CH:26]=[C:27]([CH:29]([CH3:31])[CH3:30])[N:28]=2)=[O:23])[CH:16]=[C:17]([O:19][CH3:20])[CH:18]=1>C(Cl)Cl>[C:7]([C:14]1[C:13]([O:12][CH3:11])=[CH:18][C:17]([O:19][CH3:20])=[CH:16][C:15]=1[NH:21][C:22]([C:24]1[S:25][CH:26]=[C:27]([CH:29]([CH3:31])[CH3:30])[N:28]=1)=[O:23])(=[O:9])[CH3:8]

Participants

Conditions

Temperature: 0 °C

Procedure

To a suspension of Et2AlCl (1.61 g, 12.04 mmol) in DCM at 0° C. was added acetyl chloride (630 mg, 8.02 mmol). The mixture was stirred at 0° C. for 30 min. Compound 216e (1.23 g, 4.01 mmol) was then added and the reaction mixture was stirred at 80° C. for 90 min. The reaction was poured in ice and DCM was added. The organic layers were separated, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was purified by chromatography on silica gel (EtOAc/DCM) to yield compound 217e as a white solid in 82% yield. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.41 (s, 3H), 1.43 (s, 3H), 2.63 (s, 3H), 3.20-3.27 (m, 1H), 3.89 (s, 3H), 3.90 (s, 3H), 6.27 (d, J=2.30, 1H), 7.19 (s, 1H), 8.12 (d, J=2.30 Hz, 1H).

Workup

stirringthe reaction mixture was stirred at 80° C. for 90 min
additionThe reaction was poured in ice
customThe organic layers were separated
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure
customThe crude product was purified by chromatography on silica gel (EtOAc/DCM)

Sources & evidence

ORD record: ord-98c2753829224aa6a60b4fb67dad4f58
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08377962B2

Linked notes

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