Triethylamine → 3-[5-(3,5-Difluorobenzamido)-2-methylphenyl]-6-(4-methylpiperazin-1-yl)-3,4-dihydroquinazolin-4-one

HRID 2117346Notes

Reaction equation

HRID 2117346 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5](Cl)=[O:6].[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:37])=[C:17]([N:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH:26]=3)[N:21]=[CH:20]2)[CH:18]=1.C(N(CC)CC)C>C(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[C:5]([NH:12][C:13]1[CH:14]=[CH:15][C:16]([CH3:37])=[C:17]([N:19]2[C:28](=[O:29])[C:27]3[C:22](=[CH:23][CH:24]=[C:25]([N:30]4[CH2:35][CH2:34][N:33]([CH3:36])[CH2:32][CH2:31]4)[CH:26]=3)[N:21]=[CH:20]2)[CH:18]=1)=[O:6]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1456003,5-Difluorobenzoyl chlorideHCID 222381673-(5-Amino-2-methylphenyl)-6-(4-methylpiperazin-1-yl)-3,4-dihydroquinazolin-4-one

Product 1

HCID 222381933-[5-(3,5-Difluorobenzamido)-2-methylphenyl]-6-(4-methylpiperazin-1-yl)-3,4-dihydroquinazolin-4-oneYield 97.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3,5-Difluorobenzoyl chloride (0.91 g) was added to a stirred mixture of 3-(5-amino-2-methylphenyl)-6-(4-methylpiperazin-1-yl)-3,4-dihydroquinazolin-4-one (1.5 g), triethylamine (1.04 g) and methylene chloride (50 ml) and the resultant mixture was stirred at ambient temperature for 18 hours. The mixture was washed with a saturated aqueous sodium bicarbonate solution and the organic phase was evaporated. There was thus obtained the title compound (2.04 g); NMR Spectrum: (DMSOd6) 2.05 (s, 3H), 2.22 (s, 3H), 2.45-2.5 (m, 4H), 3.24-3.3 (m, 4H), 7.41-7.56 (m, 3H), 7.61-7.68 (m, 4H), 7.75-7.79 (m, 2 H), 8.06 (s, 1H), 10.5 (s, 1H); Mass Spectrum: M+H+ 490.

Workup

  1. washThe mixture was washed with a saturated aqueous sodium bicarbonate solution
  2. customthe organic phase was evaporated

Sources & evidence

ORD record
ord-56207da1613549d88d781cbf07ae28f3
Source dataset
uspto-grants-2008_10
Patent number
US07442704B2

Reaction notes

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