Cyclobutanecarbonyl chloride → 2-(Cyclobutanecarbonylamino)-4-methylthiazole-5-carboxylic acid benzylamide

HRID 45330

Reaction equation

[CH:1]1([C:5](Cl)=[O:6])[CH2:4][CH2:3][CH2:2]1.[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:5]([CH:1]2[CH2:4][CH2:3][CH2:2]2)=[O:6])=[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 78705Cyclobutanecarbonyl chloride

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

Product 1

HCID 593696922-(Cyclobutanecarbonylamino)-4-methylthiazole-5-carboxylic acid benzylamideYield 46%

Procedure

Following the procedure as described in Example 2, making variations only as required to use cyclobutanecarbonyl 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 46% yield; 1H NMR (DMSO-ds, 300 MHz) δ 7.38-7.25 (m, 4H), 5.96 (s, br, 1H), 4.58-4.50 (m, 2H), 3.25-3.14 (m, 1H), 2.53 (s, 3H), 2.42-1.90 (m, 6H); MS (ES+) m/z 330.0 (M+1).

Sources & evidence

ORD record: ord-b7ab29657b9a43879daad28b645ddbb0
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541457B2

Linked notes

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