2-Aminothiazole → [3-Cyclopentanecarbonyl-4-(3-thiazol-2-yl-ureido)phenyl]acetic acid ethyl ester

HRID 559905Notes

Reaction equation

HRID 559905 reaction equation
[CH2:1]([O:3]C(=O)CC1C=CC(N)=CC=1)C.C1(C#N)CCCC1.[CH2:21]([O:23][C:24](=[O:40])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[C:28]([C:33]([CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:34])[CH:27]=1)[CH3:22].[NH2:41][C:42]1[S:43][CH:44]=[CH:45][N:46]=1>>[CH2:21]([O:23][C:24](=[O:40])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH2:32])=[C:28]([C:33]([CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:34])[CH:27]=1)[CH3:22].[CH2:21]([O:23][C:24](=[O:40])[CH2:25][C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:1]([NH:41][C:42]2[S:43][CH:44]=[CH:45][N:46]=2)=[O:3])=[C:28]([C:33]([CH:35]2[CH2:39][CH2:38][CH2:37][CH2:36]2)=[O:34])[CH:27]=1)[CH3:22]

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 77935CyclopentanecarbonitrileHCID 225219p-Aminophenylacetic acid ethyl esterHCID 66998892(4-Amino-3-cyclopentanecarbonylphenyl)acetic acid ethyl ester

Product 2

HCID 59732863[3-Cyclopentanecarbonyl-4-(3-thiazol-2-yl-ureido)phenyl]acetic acid ethyl esterHCID 66998892(4-Amino-3-cyclopentanecarbonylphenyl)acetic acid ethyl ester

Procedure

(4-Amino-3-cyclopentanecarbonylphenyl)acetic acid ethyl ester (2.7 g) is prepared from (4-aminophenyl)acetic acid ethyl ester (18.0 g, 0.1 mol) and cyclopentanecarbonitrile (9.5 g, 0.1 mol) following the general procedure I. [3-Cyclopentanecarbonyl-4-(3-thiazol-2-yl-ureido)phenyl]acetic acid ethyl ester (140 mg) is prepared from (4-amino-3-cyclopentanecarbonylphenyl)acetic acid ethyl ester (138 mg, 0.5 mmol) and 2-aminothiazole (0.060 g, 0.6 mmol) following the general procedure D.

Sources & evidence

ORD record
ord-3ee2dbc5b3a1445a91f4131f339600cb
Source dataset
uspto-grants-2011_11
Patent number
US08063081B2

Reaction notes

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