Ethyl 2-amino-4-methylthiazole-5-carboxylate → HCID 86689194, compound

HRID 589788Notes

Reaction equation

HRID 589788 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[CH:15]=[CH:16][C:17]2[S:21][C:20]([S:22](Cl)(=[O:24])=[O:23])=[C:19]([CH3:26])[C:18]=2[CH:27]=1>>[Cl:13][C:14]1[CH:15]=[CH:16][C:17]2[S:21][C:20]([S:22]([NH:1][C:2]3[S:3][C:4]([C:8]([O:10][CH2:11][CH3:12])=[O:9])=[C:5]([CH3:7])[N:6]=3)(=[O:24])=[O:23])=[C:19]([CH3:26])[C:18]=2[CH:27]=1

Participants

3

Reactant 2

HCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateHCID 27357565-Chloro-3-methylbenzo(b)thiophene-2-sulfonyl chloride

Product 1

HCID 86689194HCID 86689194, compoundYield 18%

Procedure

The product was prepared from ethyl 2-amino-4-methyl-1,3-thiazole-5-carboxylate (9 mg, 0.050 mmol) and 5-chloro-3-methylbenzothiophene-2-sulfonyl chloride (14 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 18% yield (3.9 mg). 1H NMR (500 MHz, CDCl3) δ ppm 1.34 (t, J=7.15 Hz, 3 H) 2.60 (s, 3 H) 2.61 (s, 3 H) 4.30 (q, J=7.15 Hz, 2 H) 7.42 (dd, J=8.63, 2.01 Hz, 1 H) 7.66 (dd, J=8.63, 0.50 Hz, 1 H) 7.70 (dd, J=2.01, 0.50 Hz, 1 H). MS (ESI+) m/z 431 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-6d4af9cf2b834e1b82c7d70d1f35418c
Source dataset
uspto-grants-2016_01
Patent number
US09233946B2

Reaction notes

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