Dimethylformamide → N-(4-1H-Imidazol-1-yl)butyl-2-(1-methylethyl)-11-oxo-11H-pyrido(2,1b)quinazoline-8-carboxamide

HRID 1583394Notes

Reaction equation

HRID 1583394 reaction equation
[CH3:1][CH:2]([C:4]1[CH:5]=[C:6]2[C:11](=[CH:12][CH:13]=1)[N:10]=[C:9]1[CH:14]=[CH:15][C:16]([C:18](OCC#N)=[O:19])=[CH:17][N:8]1[C:7]2=[O:24])[CH3:3].[N:25]1([CH:30](N)[CH2:31][CH2:32][CH3:33])[CH:29]=[CH:28][N:27]=[CH:26]1.C[N:36](C)C=O>O>[N:25]1([CH2:30][CH2:31][CH2:32][CH2:33][NH:36][C:18]([C:16]2[CH:15]=[CH:14][C:9]3[N:8]([CH:17]=2)[C:7](=[O:24])[C:6]2[C:11](=[CH:12][CH:13]=[C:4]([CH:2]([CH3:3])[CH3:1])[CH:5]=2)[N:10]=3)=[O:19])[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 13557516cyanomethyl 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylateHCID 18612370(1H-imidazol-1-yl)butanamine

Product 1

HCID 145955N-(4-1H-Imidazol-1-yl)butyl-2-(1-methylethyl)-11-oxo-11H-pyrido(2,1b)quinazoline-8-carboxamideYield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 1.30 g of cyanomethyl 2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxylate and 1.20 g of (1H-imidazol-1-yl)butanamine in 15 ml of dimethylformamide was stirred at a bath temperature of 35° C. for 18 hours. The reaction mixture was diluted with water and the crude precipitate was recrystallized from acetonitrile to give 1.41 g (85%) of N-[4-(1H-imidazol-1-yl)butyl]-2-(1-methylethyl)-11-oxo-11H-pyrido[2,1-b]quinazoline-8-carboxamide, mp 165°-167° C.

Workup

  1. customthe crude precipitate was recrystallized from acetonitrile

Sources & evidence

ORD record
ord-b6a3d336bdb74241be1bdb1d12785fdd
Source dataset
uspto-grants-1985_11
Patent number
US04551460

Reaction notes

Loading…