Benzoyl chloride → HCID 59369646, compound

HRID 45337Notes

Reaction equation

[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH2:16])=[N:13][C:12]=1[C:17]([F:20])([F:19])[F:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([NH:16][C:21](=[O:28])[C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)=[N:13][C:12]=1[C:17]([F:20])([F:18])[F:19])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Reactant 2

HCID 7412Benzoyl chloride

HCID 866425172-Amino-4-trifluoromethylthiazole-5-carboxylic acid benzylamide

Product 1

HCID 59369646HCID 59369646, compoundYield 62%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 2-amino-4-trifluoromethylthiazole-5-carboxylic acid benzylamide in place of 2-amino-4-methylthiazole-5-carboxylic acid 4-chlorobenzylamide to react with benzoyl chloride, the title compound was obtained as a white solid in 62% yield; 1H NMR (CDCl3, 300 MHz) δ 13.28 (t, J=6.2 Hz, 1H), 9.30-9.25 (m, 1H), 8.10-8.08 (m, 2H), 7.65-7.50 (m, 3H), 7.35-7.20 (m, 5H), 4.40-4.35 (m, 2H); 13C NMR (CDCl3, 75 MHz) δ 166.4, 159.5, 158.7, 139.1, 136.2, 135.7, 133.7, 131.4, 129.2, 128.8, 127.7, 127.5, 122.9, 119.3, 43.4; MS (ES+) m/z 406.1 (M+1).

Sources & evidence

ORD record: ord-88bdfc2256534d408ffae6eb2554471d
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541457B2

Reaction notes

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