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

HRID 1363741Notes

Reaction equation

HRID 1363741 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]([CH2:30][CH:31]2[CH2:35][CH2:34][CH2:33][CH2:32]2)[C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[CH:23]=2)=[O:20])=[N:15][CH:14]=1)(=[O:12])=[O:11])=[O:4].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.COC([C@@H]1CCCN1S(C1SC(N)=NC=1)(=O)=O)=O>>[CH:31]1([CH2:30][N:21]([C:22]2[CH:27]=[CH:26][C:25]([F:28])=[C:24]([F:29])[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)[CH2:32][CH2:33][CH2:34][CH2:35]1

Participants

6

Reactant 5

HCID 70106CyclopentanecarbaldehydeHCID 774693,4-DifluoroanilineHCID 57668246{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-4-yl}-acetic acidHCID 86629876(S)-1-{2-[3-cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazole-5-sulfonyl}-pyrrolidine-2-carboxylic acid methyl esterHCID 86629877(S)-1-(2-aminothiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester

Product 1

HCID 57668399(S)-1-{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazole-5-sulfonyl}-pyrrolidine-2-carboxylic acid

Procedure

The title compound was prepared via (S)-1-{2-[3-cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazole-5-sulfonyl}-pyrrolidine-2-carboxylic acid methyl 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 (S)-1-(2-amino-thiazole-5-sulfonyl)-pyrrolidine-2-carboxylic acid methyl ester.

Sources & evidence

ORD record
ord-30cace35713a454b9277aefbdbb5e937
Source dataset
uspto-grants-2011_02
Patent number
US07884210B2

Reaction notes

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