2-Chlorobenzimidazole → 2-[4-(1H-2-Benzimidazolyl)-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamine

HRID 1156021Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1156021
Cl.[NH2:2][C:3]1[C:12]2[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=2)[N:6]=[C:5]([N:17]2[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]2)[N:4]=1.Cl[C:24]1[NH:28][C:27]2[CH:29]=[CH:30][CH:31]=[CH:32][C:26]=2[N:25]=1>C(O)CCC.C(N(CC)CC)C>[NH:25]1[C:26]2[CH:32]=[CH:31][CH:30]=[CH:29][C:27]=2[N:28]=[C:24]1[N:20]1[CH2:21][CH2:22][N:17]([C:5]2[N:4]=[C:3]([NH2:2])[C:12]3[C:7](=[CH:8][C:9]([O:15][CH3:16])=[C:10]([O:13][CH3:14])[CH:11]=3)[N:6]=2)[CH2:18][CH2:19]1

Komponenten

5

Edukt 2

HCID 785722-ChlorobenzimidazoleHCID 204738332-Piperazine-4-amino-6,7-dimethoxy quinoline hydrochloride

Produkt 1

HCID 130363862-[4-(1H-2-Benzimidazolyl)-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamineAusbeute 54,7 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 2631-ButanolLösungsmittelHCID 8471TriethylamineLösungsmittel

Versuchsvorschrift

To 5.14 g of 4-amino-6,7-dimethoxy-2-(1-piperazinyl)quinazoline hydrochloride in 100 ml butanol, 11 ml of triethylamine was added. The mixture was stirred for 15 min and 2.65 g of 2-chloro-1H-benzimidazole was added. The mixture was refluxed for 18 hr and evaporated. Water was added to the residue and the residue was extracted with ethyl acetate. The ethyl acetate extract was washed with water, dried over sodium sulfate and evaporated. The residue was crystallized from methanol to give 3.5 g of the title compound, which was recrystallized from methanol: mp>250° C.; ir (nujol mull) 3360 and 3180 cm-1 ; uv max (MeOH) 341 (ε=6,300), 284 (ε=28,500) and 251 nm (ε=66,800); nmr (DMSO-d6) ε 3.5 (m, 4H), 3.8 (m, 4H), 3.8 (s, 3H), 3.84 (s, 3H), 7.1 (m, 8H) and 10.7 (s, 1H); and Anal. Calcd for C21H23N7O2. 1/2 H2O: C, 60.86% H, 5.79% N, 23.67% and Found: C, 60.87% H, 5.98% N, 23.65%.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 18 hr
  2. customevaporated
  3. additionWater was added to the residue
  4. extractionthe residue was extracted with ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. dry with materialdried over sodium sulfate
  8. customevaporated
  9. customThe residue was crystallized from methanol

Quellen und Nachweise

ORD-Eintrag
ord-8863c4fc2e30442f8bf2df359ee7ba5e
Quelldatensatz
uspto-grants-1982_06
Patentnummer
US04333937

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