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

HRID 589794Notes

Reaction equation

HRID 589794 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:11])=[C:5]([C:7]([O:9]C)=[O:8])[N:6]=1.[Cl:12][C:13]1[S:17][C:16]([S:18](Cl)(=[O:20])=[O:19])=[CH:15][C:14]=1[C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[F:29]>>[Cl:12][C:13]1[S:17][C:16]([S:18]([NH:1][C:2]2[S:3][C:4]([CH3:11])=[C:5]([C:7]([OH:9])=[O:8])[N:6]=2)(=[O:20])=[O:19])=[CH:15][C:14]=1[C:22]1[CH:27]=[C:26]([F:28])[CH:25]=[CH:24][C:23]=1[F:29]

Participants

3

Reactant 2

HCID 1132801Methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylateHCID 866891905-Chloro-4-(2,5-difluorophenyl)thiophene-2-sulfonyl chloride2×

Product 1

HCID 866892002-({[5-Chloro-4-(2,5-difluorophenyl)thiophen-2-yl]sulfonyl}amino)-5-methyl-1,3-thiazole-4-carboxylic acidYield 21%

Procedure

The product was prepared from methyl 2-amino-5-methyl-1,3-thiazole-4-carboxylate (25 mg, 0.15 mmol), and 5-chloro-4-(2,5-difluorophenyl)thiophene-2-sulfonyl chloride (Intermediate 20) (48 mg, 0.15 mmol) according to the General Procedure 11, described in Example 131. The crude product was purified using reversed phase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, gradient: H20.1% TFA in water/MeCN over 6 minutes). The title compound was obtained in 21% yield (14.1 mg). 1H NMR (400 MHz, MeOH-d4) δ ppm 2.56 (s, 3 H) 7.17-7.30 (m, 3 H) 7.55 (d, J=1.76 Hz, 1 H). MS (ESI+) m/z 451 [M+H]+.

Workup

  1. customThe crude product was purified
  2. customphase chromatography (ACE C8, 5 μm, 21×50 mm, flow 25 ml/min, gradient: H20.1% TFA in water/MeCN over 6 minutes)

Sources & evidence

ORD record
ord-b057e7aa1d26434f9315893dfe046783
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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