m-Aminoacetanilide → {2-[3-(3-Acetylamino-phenyl)-3-(3-methyl-butyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid

HRID 2043958

Reaction equation

HRID 2043958 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][S:6][C:7]1[S:11][C:10]([NH:12][C:13]([N:15]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([NH:27][C:28](=[O:30])[CH3:29])[CH:22]=2)[CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])=[O:14])=[N:9][CH:8]=1)C.C1(CN(C2C=CC(F)=C(F)C=2)C(=O)NC2SC=C(CC(O)=O)N=2)CCCC1.NC1C=C(NC(=O)C)C=CC=1.CC(C)CC=O.C(OC(=O)CSC1SC(N)=NC=1)C>>[C:28]([NH:27][C:23]1[CH:22]=[C:21]([N:15]([CH2:16][CH2:17][CH:18]([CH3:20])[CH3:19])[C:13](=[O:14])[NH:12][C:10]2[S:11][C:7]([S:6][CH2:5][C:4]([OH:31])=[O:3])=[CH:8][N:9]=2)[CH:26]=[CH:25][CH:24]=1)(=[O:30])[CH3:29]

Participants

6

Reactant 5

HCID 7604m-AminoacetanilideHCID 115523-MethylbutanalHCID 21455623Ethyl 2-(2-aminothiazol-5-ylthio)acetateHCID 57668246{2-[3-Cyclopentylmethyl-3-(3,4-difluoro-phenyl)-ureido]-thiazol-4-yl}-acetic acidHCID 86629907{2-[3-(3-Acetylamino-phenyl)-3-(3-methyl-butyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid ethyl ester

Product 1

HCID 57668406{2-[3-(3-Acetylamino-phenyl)-3-(3-methyl-butyl)-ureido]-thiazol-5-ylsulfanyl}-acetic acid

Procedure

The title compound was prepared via {2-[3-(3-acetylamino-phenyl)-3-(3-methyl-butyl)-ureido]-thiazol-5-ylsulfanyl}-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 N-(3-amino-phenyl)-acetamide, 3-methylbutanal and (2-amino-thiazol-5-ylsulfanyl)acetic acid ethyl ester.

Sources & evidence

ORD record
ord-b1e588bcb93e4d4f98a1813e31594527
Source dataset
uspto-grants-2013_11
Patent number
US08586614B2

Linked notes

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