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

HRID 589789Notes

Reaction equation

HRID 589789 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[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]([O:10][CH2:11][CH3:12])=[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 86689195Ethyl 2-({[5-chloro-4-(2,5-difluorophenyl)thiophen-2-yl]sulfonyl}amino)-4-methyl-1,3-thiazole-5-carboxylateYield 20%

Procedure

The product was prepared from ethyl 2-amino-4-methyl-1,3-thiazole-5-carboxylate (9 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 9, described in Example 123, using a slightly modified reaction temperature of 60° C. and a reaction time of one week. The title compound was obtained in 20% yield (4.7 mg). 1H NMR (500 MHz, CDCl3) δ ppm 1.36 (t, J=7.11 Hz, 3 H) 2.62 (s, 3 H) 4.32 (q, J=7.11 Hz, 2 H) 7.05-7.11 (m, 1 H) 7.13 (td, J=9.02, 4.63 Hz, 1 H) 7.16 (ddd, J=8.55, 5.62, 3.07 Hz, 1 H) 7.60 (d, J=1.83 Hz, 1 H). MS (ESI+) m/z 479 [M+H]+.

Workup

  1. customa slightly modified reaction temperature of 60° C.
  2. customa reaction time of one week

Sources & evidence

ORD record
ord-4621b2b218354a64824faf1bdd25e0d2
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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