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

HRID 2043926Notes

Reaction equation

HRID 2043926 reaction equation
C([O:3][C:4](=[O:33])[CH2:5][NH:6][S:7]([C:10]1[S:14][C:13]([NH:15][C:16]([N:18](CC2CCCC2)[C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)=[O:17])=[N:12][CH:11]=1)(=[O:9])=[O:8])C.[CH:34]1(CN(C2C=CC(F)=C(F)C=2)C(=O)NC2SC=C(CC(O)=O)N=2)[CH2:38][CH2:37][CH2:36][CH2:35]1.F[C:62]1C=C(C=CC=1F)N.C1(C=O)CCCC1.C(OC(=O)CNS(C1SC(N)=NC=1)(=O)=O)C.COC([C@@H]1CCCN1S(C1SC(N)=NC=1)(=O)=O)=O>>[CH:34]1([N:18]([C:19]2[CH:24]=[CH:23][C:22]([F:25])=[C:21]([F:26])[CH:20]=2)[C:16](=[O:17])[N:15]([CH3:62])[C:13]2[S:14][C:10]([S:7]([NH:6][CH2:5][C:4]([OH:3])=[O:33])(=[O:9])=[O:8])=[CH:11][N:12]=2)[CH2:38][CH2:37][CH2:36][CH2:35]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 86253773(2-Amino-thiazole-5-sulfonylamino)acetic acid ethyl esterHCID 86629877(S)-1-(2-aminothiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl esterHCID 86629878{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazole-5-sulfonylamino}-acetic acid ethyl ester

Product 1

HCID 67050124{2-[3-Cyclopentyl methyl-3-(3,4-difluoro-phenyl)-ureido]-thiazole-5-sulfonylamino}-acetic acid

Procedure

The title compound was prepared via {2-[3-cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazole-5-sulfonylamino}-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 3,4-difluoroaniline, cyclopentanecarbaldehyde and (2-amino-thiazole-5-sulfonylamino)acetic 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-9327bd81e5a64b49bb1762a136d627de
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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