HCID 68405739, compound → HCID 11544841, compound

HRID 2244431Notes

Reaction equation

HRID 2244431 reaction equation
C(OC([C:6]1[N:7]=[C:8]([CH:12]2[CH2:14][CH2:13]2)S[C:10]=1N)=O)C.C(O[C:18]([C:20]1[N:21]=[C:22]([CH:32]2[CH2:34][CH2:33]2)[S:23][C:24]=1[NH:25][C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1)=[O:19])C.C1(C2SC(NC3C=NC=CC=3)=C(C(O)=O)[N:42]=2)CC1>>[CH3:10][C:6]1[N:7]=[C:8]([NH:42][C:18]([C:20]2[N:21]=[C:22]([CH:32]3[CH2:33][CH2:34]3)[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:13]=1

Participants

4

Reactant 3

HCID 68405739HCID 68405739, compoundHCID 68405896HCID 68405896, compoundHCID 68408570HCID 68408570, compound

Product 1

HCID 11544841HCID 11544841, compound

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 cyclopropanecarbonyl chloride, and yielded cyano-(cyclopropanecarbonyl-amino)-acetic acid ethyl ester, which was cyclized to 5-amino-2-cyclopropyl-thiazole-4-carboxylic acid ethyl ester in step D. This was used in step E to generate 2-cyclopropyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester, which was hydrolized to 2-cyclopropyl-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-4b3befcf2cd54c0cb608c63871c78b46
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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