Ethyl 5-amino-2-isopropyl-1,3-thiazole-4-carboxylate → 2-Isopropyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid (6-methyl-pyridin-2-yl)-amide
Reaction equation
C(O[C:4]([C:6]1[N:7]=[C:8]([CH:12]([CH3:14])C)S[C:10]=1N)=O)C.C(O[C:18]([C:20]1[N:21]=[C:22]([CH:32]([CH3:34])[CH3:33])[S:23][C:24]=1[NH:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=[O:19])C.C(C1SC(NC2C=NC=CC=2)=C(C(O)=O)[N:42]=1)(C)C>>[CH3:10][C:6]1[N:7]=[C:8]([NH:42][C:18]([C:20]2[N:21]=[C:22]([CH:32]([CH3:33])[CH3:34])[S:23][C:24]=2[NH:25][C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)=[O:19])[CH:12]=[CH:14][CH:4]=1Participants
4
Reactant 3
Product 1
Procedure
The title compound, MS (ISP): m/e=352.3 (M+H+), was prepared as for example 153, steps A to G. Step C was performed using isobutyryl chloride, and yielded cyano-isobutyrylamino-acetic acid ethyl ester, which was cyclized to 5-amino-2-isopropyl-thiazole-4-carboxylic acid ethyl ester in step D. This was used in step E to generate 2-isopropyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester, which was hydrolized to 2-isopropyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid in step F. Coupling as described in step G generated the title compound.
Sources & evidence
- ORD record
- ord-e9d63ae88bbb4537bc057d65d4a15bd7
- Source dataset
- uspto-grants-2010_03
- Patent number
- US07678815B2
Reaction notes
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