HCID 68405954, compound → HCID 11631997, compound

HRID 2244432Notes

Reaction equation

HRID 2244432 reaction equation
C(OC([C:6]1[N:7]=[C:8]([CH:12]2[CH2:15][CH2:14]C2)S[C:10]=1N)=O)C.C(O[C:19]([C:21]1[N:22]=[C:23]([CH:33]2[CH2:36][CH2:35][CH2:34]2)[S:24][C:25]=1[NH:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1)=[O:20])C.C1(C2SC(NC3C=NC=CC=3)=C(C(O)=O)[N:45]=2)CCC1>>[CH3:10][C:6]1[N:7]=[C:8]([NH:45][C:19]([C:21]2[N:22]=[C:23]([CH:33]3[CH2:34][CH2:35][CH2:36]3)[S:24][C:25]=2[NH:26][C:27]2[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=2)=[O:20])[CH:12]=[CH:15][CH:14]=1

Participants

4

Reactant 3

HCID 68405954HCID 68405954, compoundHCID 68406986HCID 68406986, compoundHCID 68678007HCID 68678007, compound

Product 1

HCID 11631997HCID 11631997, compound

Procedure

The title compound, MS (ISP): m/e=366.0 (M+H+), was prepared as for example 153, steps A to G. Step C was performed using cyclobutanecarbonyl chloride, and yielded cyano-(cyclobutanecarbonyl-amino)-acetic acid ethyl ester, which was cyclized to 5-amino-2-cyclobutyl-thiazole-4-carboxylic acid ethyl ester in step D. This was used in step E to generate 2-cyclobutyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester, which was hydrolized to 2-cyclobutyl-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-143615a8d6134f3d98710c45155c20a7
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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