Pivaloyl chloride → 2-(2,2-Dimethylpropionylamino)-4-methylthiazole-5-carboxylic Acid Benzylamide

HRID 45329

Reaction equation

[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[CH2:8]([NH:15][C:16]([C:18]1[S:22][C:21]([NH2:23])=[N:20][C:19]=1[CH3:24])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([NH:15][C:16]([C:18]1[S:22][C:21]([NH:23][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[N:20][C:19]=1[CH3:24])=[O:17])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

Reactant 2

HCID 62493Pivaloyl chloride

HCID 210824N-Benzyl-2-imino-4-methyl-2,3-dihydro-1,3-thiazole-5-carboximidic acid

Product 1

HCID 593697062-(2,2-Dimethylpropionylamino)-4-methylthiazole-5-carboxylic Acid BenzylamideYield 23%

Procedure

Following the procedure as described in Example 2, making variations only as required to use 2,2-dimethylpropionyl chloride in place of benzoyl chloride to react with 2-amino-4-methylthiazole-5-carboxylic acid benzylamide, the title compound was obtained as a white solid in 23% yield; 1H NMR (CDCl3, 300 MHz) δ 8.85 (s, br, 1H), 7.36-7.25 (m, 5H), 5.91 (s, br, 1H), 4.56 (d, J=5.8 Hz, 2H), 2.60 (s, 3H), 1.27 (s, 9H); MS (ES+) m/z 332.0 (M+1).

Sources & evidence

ORD record: ord-9c5547534c57484f8d3031cb2a12717e
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541457B2

Linked notes

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