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

HRID 2043922Notes

Reaction equation

HRID 2043922 reaction equation
C([O:3][C:4](=[O:32])[C:5]([S:8][C:9]1[S:13][C:12]([NH:14][C:15]([N:17]([CH2:26][CH:27]2[CH2:31][CH2:30][CH2:29][CH2:28]2)[C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)=[O:16])=[N:11][CH:10]=1)([CH3:7])[CH3:6])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)C(SC1SC(N)=NC=1)(C)C)C>>[CH:27]1([CH2:26][N:17]([C:18]2[CH:23]=[CH:22][C:21]([F:24])=[C:20]([F:25])[CH:19]=2)[C:15](=[O:16])[NH:14][C:12]2[S:13][C:9]([S:8][C:5]([CH3:6])([CH3:7])[C:4]([OH:32])=[O:3])=[CH:10][N:11]=2)[CH2:31][CH2:30][CH2:29][CH2:28]1

Participants

6

Reactant 5

HCID 70106CyclopentanecarbaldehydeHCID 774693,4-DifluoroanilineHCID 57481427Ethyl 2-[(2-amino-1,3-thiazol-5-yl)sulfanyl]-2-methylpropanoateHCID 57668246{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-4-yl}-acetic acidHCID 866298732-{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-5-ylsulfanyl}-2-methyl-propionic acid ethyl ester

Product 1

HCID 576683642-{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-5-ylsulfanyl}-2-methyl-propionic acid

Procedure

The title compound was prepared via 2-{2-[3-cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-5-ylsulfanyl}-2-methyl-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 2-(2-amino-thiazol-5-ylsulfanyl)-2-methyl-propionic acid ethyl ester.

Sources & evidence

ORD record
ord-8a41a85b56bd4b6eae8cd952039b55d5
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Reaction notes

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