Ethyl 2-amino-4-methylthiazole-5-carboxylate → 2-({[5-Chloro-4-(2,5-difluorophenyl)thiophen-2-yl]sulfonyl}amino)-4-methyl-1,3-thiazole-5-carboxylic acid

HRID 589791Notes

Reaction equation

HRID 589791 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10]CC)=[O:9])=[C:5]([CH3:7])[N:6]=1.[Cl:13][C:14]1[S:18][C:17]([S:19](Cl)(=[O:21])=[O:20])=[CH:16][C:15]=1[C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[F:30]>>[Cl:13][C:14]1[S:18][C:17]([S:19]([NH:1][C:2]2[S:3][C:4]([C:8]([OH:10])=[O:9])=[C:5]([CH3:7])[N:6]=2)(=[O:21])=[O:20])=[CH:16][C:15]=1[C:23]1[CH:28]=[C:27]([F:29])[CH:26]=[CH:25][C:24]=1[F:30]

Participants

3

Reactant 2

HCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateHCID 866891905-Chloro-4-(2,5-difluorophenyl)thiophene-2-sulfonyl chloride2×

Product 1

HCID 866891972-({[5-Chloro-4-(2,5-difluorophenyl)thiophen-2-yl]sulfonyl}amino)-4-methyl-1,3-thiazole-5-carboxylic acidYield 17%

Procedure

The product was prepared from ethyl 2-amino-4-methylthiazole-5-carboxylate (9.3 mg, 0.050 mmol) and 5-chloro-4-(2,5-difluorophenyl)thiophene-2-sulfonyl chloride (Intermediate 20) (17 mg, 0.050 mmol) according to the General Procedure 10, described in Example 128. The title compound was obtained in 17% yield (3.9 mg). 1H NMR (500 MHz, MeOH-d4) δ ppm 2.50 (s, 3 H) 7.18-7.23 (dddd, J=9.16, 7.57, 3.91, 3.05 Hz, 1 H) 7.26 (td, J=9.16, 4.60 Hz, 1H) 7.26 (ddd, J=8.70, 5.70, 3.05 Hz, 1 H) 7.57 (d, J=1.71 Hz, 1 H). MS (ESI+) m/z 451 [M+H]+.

Sources & evidence

ORD record
ord-cfee2ae2d9954f14893faa7ed32ccdfd
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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