1-Naphthalenemethanamine → HCID 178475835, compound

HRID 1595399Notes

Reaction equation

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

Participants

Reactant 2

HCID 83551-Naphthalenemethanamine

HCID 178475845HCID 178475845, compound

Product 1

HCID 178475835HCID 178475835, compoundYield 39.7%

Procedure

tert-Butyl 3-(4-acetoxymethylphenyl)-2-hydroxyimino-3-oxopropionate (19.2 g) and 1-naphthylmethylamine (11.3 g) were reacted and treated in the same manner as in Starting Material Synthetic Example 1 to give tert-butyl 5-(4-acetoxymethylphenyl)-2-(1-naphthyl)-imidazole-4-carboxylate (10.5 g), melting point 162-164° C. (2) tert-Butyl 5-(4-acetoxymethylphenyl)-2-(1-naphthyl)imidazole-4-carboxylate (10.5 g) was reacted and treated in the same manner as in Example 31 to give 5-(4-acetoxymethylphenyl)-2-(1-naphthyl)-N-(2-thiazolyl)imidazole-4-carboxamide (6.62 g), melting point 197-199° C.

Workup

additiontreated in the same manner as

Sources & evidence

ORD record: ord-811d48bdb79f437189f7cf8fea29c1f4
Source dataset: uspto-grants-2001_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06288061B1

Reaction notes

Loading…