Cyclopentylmethyl-(4-methanesulfonyl-phenyl)-amine → 3-{2-[3-Cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]-thiazole-5-sulfonylamino}-propionic acid

HRID 2043935Notes

Reaction equation

HRID 2043935 reaction equation
C([O:3][C:4](=[O:36])[CH2:5][CH2:6][NH:7][S:8]([C:11]1[S:15][C:14]([NH:16][C:17]([N:19]([CH2:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:28])=[O:27])=[CH:22][CH:21]=2)=[O:18])=[N:13][CH:12]=1)(=[O:10])=[O:9])C.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.C(OC(=O)CCNS(C1SC(N)=NC=1)(=O)=O)C.COC([C@@H]1CCCN1S(C1SC(N)=NC=1)(=O)=O)=O>>[CH:31]1([CH2:30][N:19]([C:20]2[CH:25]=[CH:24][C:23]([S:26]([CH3:29])(=[O:27])=[O:28])=[CH:22][CH:21]=2)[C:17](=[O:18])[NH:16][C:14]2[S:15][C:11]([S:8]([NH:7][CH2:6][CH2:5][C:4]([OH:36])=[O:3])(=[O:10])=[O:9])=[CH:12][N:13]=2)[CH2:35][CH2:34][CH2:33][CH2:32]1

Participants

6

Reactant 5

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 866298803-(2-Amino-thiazole-5-sulfonylamino)propionic acid ethyl esterHCID 866298853-{2-[3-Cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]-thiazole-5-sulfonylamino}-propionic acid ethyl ester

Product 1

HCID 576684103-{2-[3-Cyclopentylmethyl-3-(4-methanesulfonyl-phenyl)-ureido]-thiazole-5-sulfonylamino}-propionic acid

Procedure

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

Sources & evidence

ORD record
ord-a8f8f4ff0673451c9b61915dfaa96a30
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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