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

HRID 1156021Notes

Reaction equation

HRID 1156021 reaction equation
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

Participants

5

Reactant 2

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

Product 1

HCID 130363862-[4-(1H-2-Benzimidazolyl)-1-piperazinyl]-6,7-dimethoxy-4-quinazolinamineYield 54.7%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 8471TriethylamineSolvent

Procedure

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%.

Workup

  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

Sources & evidence

ORD record
ord-8863c4fc2e30442f8bf2df359ee7ba5e
Source dataset
uspto-grants-1982_06
Patent number
US04333937

Reaction notes

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