N-(2-acetyl-5-methoxyphenyl)-4-Isopropyl-2-Thiazolecarboxamide → N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-isopropylthiazole-2-carboxamide

HRID 388663Notes

Reaction equation

HRID 388663 reaction equation
[NH2:1][C:2]1[C:7]([Cl:8])=[C:6]([O:9][CH3:10])[CH:5]=[CH:4][C:3]=1[C:11](=[O:13])[CH3:12].[CH:14]([C:17]1[N:18]=[C:19]([C:22](Cl)=[O:23])[S:20][CH:21]=1)([CH3:16])[CH3:15].C(C1C=CC(OC)=CC=1NC(C1SC=C(C(C)C)N=1)=O)(=O)C>>[C:11]([C:3]1[C:2]([NH:1][C:22]([C:19]2[S:20][CH:21]=[C:17]([CH:14]([CH3:16])[CH3:15])[N:18]=2)=[O:23])=[C:7]([Cl:8])[C:6]([O:9][CH3:10])=[CH:5][CH:4]=1)(=[O:13])[CH3:12]

Participants

4

Reactant 3

HCID 20773655N-(2-acetyl-5-methoxyphenyl)-4-Isopropyl-2-ThiazolecarboxamideHCID 299199881-(2-Amino-3-chloro-4-methoxyphenyl)ethanoneHCID 575787964-(Propan-2-yl)-1,3-thiazole-2-carbonyl chloride

Product 1

HCID 56605150N-(6-acetyl-2-chloro-3-methoxyphenyl)-4-isopropylthiazole-2-carboxamideYield 80%

Procedure

N-(6-Acetyl-2-chloro-3-methoxyphenyl)-4-isopropylthiazole-2-carboxamide 217d was synthesized from 1-(2-amino-3-chloro-4-methoxyphenyl)ethanone and compound 214 as a beige solid in 80% yield, according to the procedure as described for compound 217a. 1H NMR (CDCl3, 400 MHz) δ (ppm) 1.47 (s, 3H), 1.48 (s, 3H), 2.57 (s, 3H), 3.34-3.41 (quint, J=6.90 Hz, 1H), 3.98 (s, 3H), 6.86 (d, J=8.48 Hz, 1H), 7.64 (d, J=8.48 Hz, 1H), 8.07 (s, 1H); MS (ESI, EI−) m/z=351 (MH−); MS (ESI, EI+): m/z=353 (MH+).

Sources & evidence

ORD record
ord-ee31b8ce6c984b3d8c1f8ecc933495fe
Source dataset
uspto-grants-2013_02
Patent number
US08377962B2

Reaction notes

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