Cyclopentylmethyl-(4-methanesulfonyl-phenyl)-amine → (S)-1-{2-[3-Cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]-thiazole-5-sulfonyl}-pyrrolidine-2-carboxylic acid

HRID 2043933Notes

Reaction equation

HRID 2043933 reaction equation
C[O:2][C:3]([C@@H:5]1[CH2:9][CH2:8][CH2:7][N:6]1[S:10]([C:13]1[S:17][C:16]([NH:18][C:19]([N:21]([CH2:32][CH:33]2[CH2:37][CH2:36][CH2:35][CH2:34]2)[C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=2)=[O:20])=[N:15][CH:14]=1)(=[O:12])=[O:11])=[O:4].C1(CN(C2C=CC(S(C)(=O)=O)=CC=2)C(=O)NC2SC=C(CC(O)=O)N=2)CCCC1.C1(CNC2C=CC(S(C)(=O)=O)=CC=2)CCCC1.COC([C@@H]1CCCN1S(C1SC(N)=NC=1)(=O)=O)=O>>[CH:33]1([CH2:32][N:21]([C:22]2[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:29])=[O:30])=[CH:24][CH:23]=2)[C:19](=[O:20])[NH:18][C:16]2[S:17][C:13]([S:10]([N:6]3[CH2:7][CH2:8][CH2:9][C@H:5]3[C:3]([OH:4])=[O:2])(=[O:12])=[O:11])=[CH:14][N:15]=2)[CH2:34][CH2:35][CH2:36][CH2:37]1

Participants

5

Reactant 4

HCID 43453307Cyclopentylmethyl-(4-methanesulfonyl-phenyl)-amineHCID 57668194{2-[3-Cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]thiazol-4-yl}-acetic acidHCID 86629877(S)-1-(2-aminothiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 86629883(S)-1-{2-[3-cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]-thiazole-5-sulfonyl}-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 58206874(S)-1-{2-[3-Cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]-thiazole-5-sulfonyl}-pyrrolidine-2-carboxylic acid

Procedure

The title compound was prepared via (S)-1-{2-[3-cyclopentylmethyl-3-(4-methanesulfonylphenyl)-ureido]-thiazole-5-sulfonyl}-pyrrolidine-2-carboxylic acid methyl ester in a similar manner as described for the synthesis of {2-[3-cyclopentylmethyl-3-(4-methanesulfonylphenyl)-ureido]-thiazol-4-yl}-acetic acid, using cyclopentylmethyl-(4-methanesulfonyl-phenyl)amine and (S)-1-(2-amino-thiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester.

Sources & evidence

ORD record
ord-8f81972e28654f129ca3e95d6e676685
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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