Isonicotinoyl chloride hydrochloride → N-[5-(4-Chlorobenzylcarbamoyl)-4-methylthiazol-2-yl]isonicotinamide

HRID 45336Notes

Reaction equation

HRID 45336 reaction equation
Cl.[C:2](Cl)(=[O:9])[C:3]1[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=1.[Cl:11][C:12]1[CH:28]=[CH:27][C:15]([CH2:16][NH:17][C:18]([C:20]2[S:24][C:23]([NH2:25])=[N:22][C:21]=2[CH3:26])=[O:19])=[CH:14][CH:13]=1>>[Cl:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][NH:17][C:18]([C:20]2[S:24][C:23]([NH:25][C:2](=[O:9])[C:3]3[CH:8]=[CH:7][N:6]=[CH:5][CH:4]=3)=[N:22][C:21]=2[CH3:26])=[O:19])=[CH:27][CH:28]=1

Participants

3

Reactant 2

HCID 12262826Isonicotinoyl chloride hydrochlorideHCID 627933982-Amino-4-methylthiazole-5-carboxylic Acid 4-Chlorobenzylamide

Product 1

HCID 59369704N-[5-(4-Chlorobenzylcarbamoyl)-4-methylthiazol-2-yl]isonicotinamideYield 99%

Procedure

Following the procedure as described in Example 2, making variations only as required to use isonicotinoyl chloride hydrochloride in place of benzoyl chloride to react with 2-amino-4-methylthiazole-5-carboxylic acid 4-chlorobenzylamide, the title compound was obtained as a white solid in 99% yield; 1H NMR (DMSO-d6, 300 MHz) δ 8.75-8.73 (m, 2H), 7.95-7.93 (m, 2H), 7.34 (s, 2H), 7.31 (s; 2H), 4.86 (s, 2H), 2.54 (s, 3H); MS (ES+) m/z 387.0 (M+1).

Sources & evidence

ORD record
ord-c6a92a9b36f24f12966a20c43970fad3
Source dataset
uspto-grants-2013_09
Patent number
US08541457B2

Reaction notes

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