Cyclopropanecarbonyl chloride → 2-(Cyclopropanecarbonylamino)-4-methylthiazole-5-carboxylic Acid 4-Chlorobenzylamide

HRID 45335Notes

Reaction equation

[CH:1]1([C:4](Cl)=[O:5])[CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:24]=[CH:23][C:11]([CH2:12][NH:13][C:14]([C:16]2[S:20][C:19]([NH2:21])=[N:18][C:17]=2[CH3:22])=[O:15])=[CH:10][CH:9]=1>>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([CH2:12][NH:13][C:14]([C:16]2[S:20][C:19]([NH:21][C:4]([CH:1]3[CH2:3][CH2:2]3)=[O:5])=[N:18][C:17]=2[CH3:22])=[O:15])=[CH:23][CH:24]=1

Participants

Reactant 2

HCID 77637Cyclopropanecarbonyl chloride

HCID 627933982-Amino-4-methylthiazole-5-carboxylic Acid 4-Chlorobenzylamide

Product 1

HCID 593696942-(Cyclopropanecarbonylamino)-4-methylthiazole-5-carboxylic Acid 4-ChlorobenzylamideYield 55%

Procedure

Following the procedure as described in Example 2, making variations only as required to use cyclopropanecarbonyl chloride 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 55% yield; 1H NMR (DMSO-d6, 300 MHz) δ 8.51 (t, J=6.0 Hz, 1H), 7.36-7.25 (m, 4H), 4.32 (d, J=6.0 Hz, 2H), 2.50 (s, 3H), 1.94-1.84 (m, 1H), 0.93-0.87 (m, 4H); MS (ES+) m/z 350.1 (M+1).

Sources & evidence

ORD record: ord-979e88832d1147ba80a12c6920eb9cf4
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08541457B2

Reaction notes

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