HCID 58333961, compound → HCID 11688944, compound

HRID 2244434Notes

Reaction equation

HRID 2244434 reaction equation
C(OC([C:6]1[N:7]=[C:8]([CH2:12][CH2:13][CH3:14])S[C:10]=1N)=O)C.C(O[C:18]([C:20]1[N:21]=[C:22]([CH2:32][CH2:33][CH3:34])[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)CC>>[CH3:10][C:6]1[N:7]=[C:8]([NH:42][C:18]([C:20]2[N:21]=[C:22]([CH2:32][CH2:33][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:13][CH:14]=1

Participants

4

Reactant 3

HCID 58333961HCID 58333961, compoundHCID 68406885HCID 68406885, compoundHCID 68407216HCID 68407216, compound

Product 1

HCID 11688944HCID 11688944, compound

Procedure

The title compound, MS (ISP): m/e=354.0 (M+H+), was prepared as for example 153, steps A to G. Step C was performed using butyryl chloride, and yielded butyrylamino-cyano-acetic acid ethyl ester, which was cyclized to 5-amino-2-propyl-thiazole-4-carboxylic acid ethyl ester in step D. This was used in step E to generate 2-propyl-5-(pyridin-3-ylamino)-thiazole-4-carboxylic acid ethyl ester, which was hydrolized to 2-propyl-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-2f881e88540d4fe89ddb5f62bcc1c173
Source dataset
uspto-grants-2010_03
Patent number
US07678815B2

Reaction notes

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