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

HRID 2084005

Reaktionsgleichung

Reaktionsgleichung von HRID 2084005
[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

Komponenten

4

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

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), 7.18 (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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-3500dcb2c4c5456b899bc320995202fe
Quelldatensatz
uspto-grants-2004_04
Patentnummer
US06716847B2

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