Cyclopentanecarbaldehyde → {2-[3-Cyclopentylmethyl-3-(3-propionylamino-phenyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid

HRID 2043982Notes

Reaction equation

HRID 2043982 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][S:6][C:7]1[S:11][C:10]([NH:12][C:13]([N:15]([CH2:27][CH:28]2[CH2:32][CH2:31][CH2:30][CH2:29]2)[C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23](=[O:26])[CH2:24][CH3:25])[CH:17]=2)=[O:14])=[N:9][CH:8]=1)C.C1(CN(C2C=CC(F)=C(F)C=2)C(=O)NC2SC=C(CC(O)=O)N=2)CCCC1.NC1C=C(NC(=O)CC)C=CC=1.C1(C=O)CCCC1.C(OC(=O)CSC1SC(N)=NC=1)C>>[CH:28]1([CH2:27][N:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([NH:22][C:23](=[O:26])[CH2:24][CH3:25])[CH:17]=2)[C:13](=[O:14])[NH:12][C:10]2[S:11][C:7]([S:6][CH2:5][C:4]([OH:33])=[O:3])=[CH:8][N:9]=2)[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

6

Reactant 5

HCID 70106CyclopentanecarbaldehydeHCID 89953N-(3-Aminophenyl)propanamideHCID 21455623Ethyl 2-(2-aminothiazol-5-ylthio)acetateHCID 57668246{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-4-yl}-acetic acidHCID 86629930{2-[3-Cyclopentylmethyl-3-(3-propionylamino-phenyl)ureido]-thiazol-5-ylsulfanyl}-acetic acid ethyl ester

Product 1

HCID 57668272{2-[3-Cyclopentylmethyl-3-(3-propionylamino-phenyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid

Procedure

The title compound was prepared via {2-[3-cyclopentylmethyl-3-(3-propionylamino-phenyl)ureido]-thiazol-5-ylsulfanyl}-acetic acid ethyl ester in a similar manner as described for the synthesis of {2-[3-cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-4-yl}-acetic acid, using N-(3-amino-phenyl)-propionamide, cyclopentanecarbaldehyde and (2-amino-thiazol-5-ylsulfanyl)acetic acid ethyl ester.

Sources & evidence

ORD record
ord-fc2a2046fd81422f818741df47673e41
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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