3-Dimethylaminobenzoyl chloride → 4-[2-Methyl-5-(3-dimethylaminobenzamido)anilino]-6,7,8-trimethoxyquinazoline

HRID 1357686

Reaction equation

HRID 1357686 reaction equation
[CH3:1][N:2]([CH3:12])[C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6](Cl)=[O:7].[CH3:13][C:14]1[CH:36]=[CH:35][C:34]([NH2:37])=[CH:33][C:15]=1[NH:16][C:17]1[C:26]2[C:21](=[C:22]([O:31][CH3:32])[C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1>C(Cl)Cl>[CH3:13][C:14]1[CH:36]=[CH:35][C:34]([NH:37][C:6](=[O:7])[C:5]2[CH:9]=[CH:10][CH:11]=[C:3]([N:2]([CH3:12])[CH3:1])[CH:4]=2)=[CH:33][C:15]=1[NH:16][C:17]1[C:26]2[C:21](=[C:22]([O:31][CH3:32])[C:23]([O:29][CH3:30])=[C:24]([O:27][CH3:28])[CH:25]=2)[N:20]=[CH:19][N:18]=1

Participants

4

Reactant 2

HCID 70103423-Dimethylaminobenzoyl chlorideHCID 227322614-(2-Methyl-5-aminoanilino)-6,7,8-trimethoxyquinazoline

Product 1

HCID 227322894-[2-Methyl-5-(3-dimethylaminobenzamido)anilino]-6,7,8-trimethoxyquinazolineYield 12%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3-Dimethylaminobenzoyl chloride (105 mg) was added to a suspension of 4-(2-methyl-5-aminoanilino)-6,7,8-trimethoxyquinazoline (180 mg) in dry methylene chloride (4 ml) and the resulting mixture was stirred at ambient temperature for 18 hours. Methylene chloride (100 ml) was added and the mixture washed with aqueous sodium hydroxide solution (100 ml), water and brine, dried over sodium sulphate, filtered and evaporated give a yellow gum. This was purified by silica column chromatography, eluting with 2% methanol in methylene chloride to yield the title compound as a solid (30 mg, 12%); NMR (CDCl3) 2.22 (s, 3H), 2.97 (s, 6H), 3.96 (s, 3H), 4.06 (s, 3H), 4.13 (s, 3H), 6.84 (dd, 1H), 7.05 (m, 2H), 2.22 (m, 2H), 7.28 (t, 1H), 7.42 (m, 1H), 7.92 (s, 1H), 7.95 (s, 1H), 8.61 (s, 1H); m/s: M+H+ 488.

Workup

  1. washthe mixture washed with aqueous sodium hydroxide solution (100 ml), water and brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated
  5. customgive a yellow gum
  6. customThis was purified by silica column chromatography
  7. washeluting with 2% methanol in methylene chloride

Sources & evidence

ORD record
ord-306ce44d10b741a19b428d3e3f598445
Source dataset
uspto-grants-2003_07
Patent number
US06593333B1

Linked notes

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