Triethylamine → 2-[4-(4-Amino-6,7-dimethoxyquinazolin-2-yl)-1-piperazinyl]-2,4,6-cycloheptatrien-1-one

HRID 1156013

Reaktionsgleichung

Reaktionsgleichung von HRID 1156013
[N:1]1([C:7]2[N:16]=[C:15]([NH2:17])[C:14]3[C:9](=[CH:10][C:11]([O:20][CH3:21])=[C:12]([O:18][CH3:19])[CH:13]=3)[N:8]=2)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.C(N(CC)CC)C.C[O:30][C:31]1[C:32](=O)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1>C(O)CCC>[NH2:17][C:15]1[C:14]2[C:9](=[CH:10][C:11]([O:20][CH3:21])=[C:12]([O:18][CH3:19])[CH:13]=2)[N:8]=[C:7]([N:1]2[CH2:6][CH2:5][N:4]([C:37]3[C:31](=[O:30])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:3][CH2:2]2)[N:16]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 165462-Methoxy-2,4,6-cycloheptatrien-1-oneHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Produkt 1

HCID 130363772-[4-(4-Amino-6,7-dimethoxyquinazolin-2-yl)-1-piperazinyl]-2,4,6-cycloheptatrien-1-oneAusbeute 51,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 2631-ButanolLösungsmittel

Versuchsvorschrift

A suspension of 2-(1-piperazinyl)-4-amino-6,7-dimethoxyquinazoline (2.48 g, prepared as described by T. H. Althuis and H.-J. Hess, J. Med. Chem., cited above), triethylamine (2.3 g) in butanol (190 ml) was stirred at room temperature for 2 hr and 2-methoxy-2,4,6-cycloheptatrien-1-one (2.06 g) was added. The mixture was refluxed for 48 hr, evaporated and chromatographed through silica gel using dichloromethane-methanol (9:1). The appropriate fractions were evaporated to give 1.73 g of the title compound. The latter material was stirred for 2 hr in a solution of hydrogen chloride in methanol and evaporated. The residue was crystallized from dichloromethane-methanol to give the title compound as the hydrochloride salt (0.835 g): mp 220°-224° C.; uv max (MeOH) 246 (ε=51740) and 343 nm (ε=25525); nmr (DMSO-d6) δ 3.55 (m, 4H), 3.85 (s, 6H), 4.05 (m, 4H), 7.0 (m, 5H), 7.75 (s, 1H) and 7.85 (s, 1H); and Anal. Calcd for C21H23N5O3.HCl: C, 58.66% H, 5.63% N, 16.29% and Found: C, 57.62% H, 5.50% N, 16.38% H2O, 1.86%.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 48 hr
  2. customevaporated
  3. customchromatographed through silica gel
  4. customThe appropriate fractions were evaporated

Quellen und Nachweise

ORD-Eintrag
ord-28da60eb8a054b5798a5847ef9e92728
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04333937

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