4-Thiazoleacetic acid, 2-amino-, ethyl ester → {2-[3-Cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]thiazol-4-yl}-acetic acid

HRID 2043930Notes

Reaction equation

HRID 2043930 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][C:6]1[N:7]=[C:8]([NH:11][C:12]([N:14]([CH2:25][CH:26]2[CH2:30][CH2:29][CH2:28][CH2:27]2)[C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:23])=[O:22])=[CH:17][CH:16]=2)=[O:13])[S:9][CH:10]=1)C.C1(CN(C2C=CC(F)=C(F)C=2)C(=O)NC2SC=C(CC(O)=O)N=2)CCCC1.C1(CNC2C=CC(S(C)(=O)=O)=CC=2)CCCC1.C(OC(=O)CC1N=C(N)SC=1)C>>[CH:26]1([CH2:25][N:14]([C:15]2[CH:20]=[CH:19][C:18]([S:21]([CH3:24])(=[O:22])=[O:23])=[CH:17][CH:16]=2)[C:12](=[O:13])[NH:11][C:8]2[S:9][CH:10]=[C:6]([CH2:5][C:4]([OH:31])=[O:3])[N:7]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 4

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 43453307Cyclopentylmethyl-(4-methanesulfonyl-phenyl)-amineHCID 57668246{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-4-yl}-acetic acidHCID 86761279{2-[3-Cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]-thiazol-4-yl}-acetic acid ethyl ester

Product 1

HCID 57668194{2-[3-Cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]thiazol-4-yl}-acetic acid

Procedure

The title compound was prepared via {2-[3-cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)ureido]-thiazol-4-yl}-acetic acid ethyl ester employing the coupling and hydrolysis protocol used for the synthesis of {2-[3-cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-4-yl}-acetic acid, using cyclopentylmethyl-(4-methanesulfonyl-phenyl)-amine and (2-amino-thiazol-4-yl)-acetic acid ethyl ester.

Workup

  1. customthe coupling and hydrolysis protocol

Sources & evidence

ORD record
ord-8ad0c41b39a74164b13baa12d0e54478
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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