Triethylamine → HCID 22732277, compound

HRID 2084003Notes

Reaction equation

HRID 2084003 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:6]([Cl:8])=[O:7].C(N(CC)CC)C.[NH2:21][C:22]1[CH:23]=[C:24]([CH:40]=[CH:41][C:42]=1[Cl:43])[NH:25][C:26]1[C:35]2[C:30](=[CH:31][C:32]([O:38][CH3:39])=[C:33]([O:36][CH3:37])[CH:34]=2)[N:29]=[CH:28][N:27]=1>C(Cl)Cl>[ClH:8].[Cl:43][C:42]1[CH:41]=[CH:40][C:24]([NH:25][C:26]2[C:35]3[C:30](=[CH:31][C:32]([O:38][CH3:39])=[C:33]([O:36][CH3:37])[CH:34]=3)[N:29]=[CH:28][N:27]=2)=[CH:23][C:22]=1[NH:21][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([O:12][CH3:13])=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 77070Veratroyl chlorideHCID 22732320HCID 22732320, compound

Product 1

HCID 22732277HCID 22732277, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

3,4-Dimethoxybenzoyl chloride (200 mg) and triethylamine (0.125 ml) were added to a suspension of 4-(3-amino-4-chloroanilino)-6,7-dimethoxyquinazoline (150 mg) in dry methylene chloride (3 ml) and the mixture was stirred at ambient temperature for 18 hours. The reaction mixture was diluted with methylene chloride and washed with water and brine and evaporated. The residue was triturated with diethyl ether (3×100 ml). The resulting solid was stirred in ethereal hydrogen chloride at ambient temperature for 18 hours and the mixture was evaporated to dryness. The resulting solid was triturated with isohexane and dried under vacuum. The title compound was obtained as a solid (30 mg); NMR: 3.85 (s, 6H), 3.92 (s, 3H), 3.96 (s, 3H), 6.98 (m, 1H), 7.32 (s, 1H), 7.45 (m, 2H), 7.99 (m, 1H), 8.15 (s, 1H), 8.88 (s, 1H), 9.98 (s, 1H), 11.32 (s, 1H); m/s: M+H+ 495, 497.

Workup

  1. washwashed with water and brine
  2. customevaporated
  3. customThe residue was triturated with diethyl ether (3×100 ml)
  4. stirringThe resulting solid was stirred in ethereal hydrogen chloride at ambient temperature for 18 hours
  5. customthe mixture was evaporated to dryness
  6. customThe resulting solid was triturated with isohexane
  7. customdried under vacuum

Sources & evidence

ORD record
ord-25b18c762ecb4fceaba32a23823388d5
Source dataset
uspto-grants-2004_04
Patent number
US06716847B2

Reaction notes

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