4-Thiazoleacetic acid, 2-amino-, ethyl ester → HCID 59732890, compound

HRID 2276253Notes

Reaction equation

HRID 2276253 reaction equation
[CH:1]1([O:6][C:7]2[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:8]=2[NH2:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:15](OC(=O)CC1N=C(N)SC=1)C.[CH2:27]([O:29][C:30](=[O:53])[CH2:31][C:32]1[N:33]=[C:34]([NH:37][C:38]([NH:40][C:41]2[CH:46]=[CH:45][C:44]([CH3:47])=[CH:43][C:42]=2[O:48][CH2:49][CH:50]2[CH2:52][CH2:51]2)=[O:39])[S:35][CH:36]=1)[CH3:28]>>[CH2:27]([O:29][C:30](=[O:53])[CH2:31][C:32]1[N:33]=[C:34]([NH:37][C:38]([NH:9][C:8]2[CH:10]=[CH:11][C:12]([CH3:14])=[CH:13][C:7]=2[O:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[O:39])[S:35][CH:36]=1)[CH3:28].[CH:49]1([O:48][C:42]2[CH:43]=[C:44]([CH3:47])[CH:45]=[CH:46][C:41]=2[NH:40][C:38](=[O:39])[NH:37][C:34]2[S:35][CH:36]=[C:32]([CH2:31][C:30]([OH:29])=[O:53])[N:33]=2)[CH2:15][CH2:51][CH2:52][CH2:50]1

Participants

5

Reactant 3

HCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 247098162-(Cyclopentyloxy)-4-methylanilineHCID 86593080HCID 86593080, compound

Product 2

HCID 59732890HCID 59732890, compoundYield 91%HCID 86593079HCID 86593079, compoundYield 62%

Procedure

{2-[3-(2-Cyclopentyloxy-4-methyl-phenyl)-ureido]-thiazol-4-yl}-acetic acid ethyl ester (250 mg, 62%) was prepared from 2-cyclopentyloxy-4-methyl-aniline (191 mg, 1.0 mmol) and (2-amino-thiazol-4-yl)-acetic acid ethyl ester (186 mg, 1.0 mmol) following the general procedure D. {2-[3-(2-Cyclopentyloxy-4-methyl-phenyl)-ureido]-thiazol-4-yl}-acetic acid (170 mg, 91%) was prepared from {2-[3-(2-cyclopropylmethoxy-4-methyl-phenyl)-ureido]-thiazol-4-yl}-acetic acid ethyl ester (200 mg, 0.5 mmol) following the general procedure J.

Sources & evidence

ORD record
ord-8ea02065b8684984ab86eba536262c77
Source dataset
uspto-grants-2015_09
Patent number
USRE045670E1

Reaction notes

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