Cyclopentylacetic acid → HCID 18360270, compound

HRID 382434Notes

Reaction equation

[NH2:1][C:2]1[N:3]=[CH:4][N:5]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([CH3:20])([CH3:19])[CH3:18])=[CH:13][CH:12]=2)[C:6]=1[C:7]([NH2:9])=[O:8].[C:21]([O:25][C:26]([N:28]([C:30]1[CH:38]=[CH:37][C:33]([C:34](O)=[O:35])=[CH:32][CH:31]=1)[CH3:29])=[O:27])([CH3:24])([CH3:23])[CH3:22].C1(CC(O)=O)CCCC1>>[C:17]([C:14]1[CH:15]=[CH:16][C:11]([CH2:10][N:5]2[C:6]([C:7]([NH2:9])=[O:8])=[C:2]([NH:1][C:34](=[O:35])[C:33]3[CH:32]=[CH:31][C:30]([N:28]([C:26]([O:25][C:21]([CH3:23])([CH3:22])[CH3:24])=[O:27])[CH3:29])=[CH:38][CH:37]=3)[N:3]=[CH:4]2)=[CH:12][CH:13]=1)([CH3:20])([CH3:19])[CH3:18]

Participants

Reactant 3

HCID 71606Cyclopentylacetic acid

HCID 111727624-[(tert-Butoxycarbonyl)(methyl)amino]benzoic acid

HCID 183602894-Amino-1-(4-t-butylbenzyl)-5-imidazolecarboxamide

Product 1

HCID 18360270HCID 18360270, compoundYield 55%

Procedure

An amidation reaction and post-treatment were carried out under the same conditions as in Example 19, using 2.65 g (9.71 mmol) of 4-amino-1-(4-t-butylbenzyl)-5-imidazolecarboxamide which was prepared in the same manner as in Example 57 and 4-(N-t-butyloxycarbonyl-N-methylamino)benzoic acid which was prepared seperately by a conventional method instead of cyclopentyl acetic acid to obtain 2.69 g of 1-(4-t-butylbenzyl)-4-(4-(N-t-butyloxycarbonyl-N-methylamino)benzoylamino)-5-imidazolecarboxamide (yield 55%).

Workup

customAn amidation reaction

Sources & evidence

ORD record: ord-4a73dcb69d074cf1b817c9005c24617b
Source dataset: uspto-grants-2001_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06310070B1

Reaction notes

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