Cyclopentanecarbaldehyde → 3-{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazole-5-sulfonylamino}-propionic acid

HRID 2043927Notes

Reaction equation

HRID 2043927 reaction equation
C([O:3][C:4](=[O:34])[CH2:5][CH2:6][NH:7][S:8]([C:11]1[S:15][C:14]([NH:16][C:17]([N:19]([CH2:28][CH:29]2[CH2:33][CH2:32][CH2:31][CH2:30]2)[C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[CH:21]=2)=[O:18])=[N:13][CH:12]=1)(=[O:10])=[O:9])C.C1(CN(C2C=CC(F)=C(F)C=2)C(=O)NC2SC=C(CC(O)=O)N=2)CCCC1.FC1C=C(C=CC=1F)N.C1(C=O)CCCC1.C(OC(=O)CCNS(C1SC(N)=NC=1)(=O)=O)C.COC([C@@H]1CCCN1S(C1SC(N)=NC=1)(=O)=O)=O>>[CH:29]1([CH2:28][N:19]([C:20]2[CH:25]=[CH:24][C:23]([F:26])=[C:22]([F:27])[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:34])=[O:3])(=[O:10])=[O:9])=[CH:12][N:13]=2)[CH2:33][CH2:32][CH2:31][CH2:30]1

Participants

7

Reactant 6

HCID 70106CyclopentanecarbaldehydeHCID 774693,4-DifluoroanilineHCID 57668246{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-4-yl}-acetic acidHCID 86629877(S)-1-(2-aminothiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 866298793-{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)ureido]-thiazole-5-sulfonylamino}-propionic acid ethyl esterHCID 866298803-(2-Amino-thiazole-5-sulfonylamino)propionic acid ethyl ester

Product 1

HCID 576683423-{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazole-5-sulfonylamino}-propionic acid

Procedure

The title compound was prepared via 3-{2-[3-cyclopentylmethyl-3-(3,4-difluoro-phenyl)ureido]-thiazole-5-sulfonylamino}-propionic 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 3,4-difluoroaniline, cyclopentanecarbaldehyde 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-1785a3534c44437cb29e8f8b0ce0df0a
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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