Triethylamine → HCID 13036373, compound

HRID 1703169Notes

Reaction equation

HRID 1703169 reaction equation
Cl.Cl[C:3]1[CH:4]=[CH:5][C:6]2[C:7](=[CH:17][CH:18]=1)[N:8]=[C:9]([N:11]1[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]1)[N:10]=2.C(N(CC)CC)C.Cl[C:27]1[N:36]=[C:35]([NH2:37])[C:34]2[C:29](=[CH:30][C:31]([O:40][CH3:41])=[C:32]([O:38][CH3:39])[CH:33]=2)[N:28]=1>C(O)CCC>[N:8]1[C:7]2=[CH:17][CH:18]=[CH:3][CH:4]=[CH:5][C:6]2=[N:10][C:9]=1[N:11]1[CH2:16][CH2:15][N:14]([C:27]2[N:36]=[C:35]([NH2:37])[C:34]3[C:29](=[CH:30][C:31]([O:40][CH3:41])=[C:32]([O:38][CH3:39])[CH:33]=3)[N:28]=2)[CH2:13][CH2:12]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 902352-Chloro-6,7-dimethoxy-4-quinazolinamineHCID 13036372HCID 13036372, compound

Product 1

HCID 13036373HCID 13036373, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 2-(1-piperazinyl)cycloheptimidazole hydrochloride (4.53 g, described in Example 1) and triethylamine (3.64 g) in butanol (500 ml) was stirred for one hr and 2-chloro-4-amino-6,7-dimethoxyquinazoline [4.35 g, prepared as described by T. H. Althuis and H.-J. Hess, J. Med. Chem., 20, 146 (1977)] was added. The mixture was refluxed for 18 hr. The resulting precipitate was collected on a filter. The filtrate was evaporated to dryness. A suspension of the precipitate and the evaporated filtrate in a cold, aqueous solution of sodium bicarbonate (5% w/v) was stirred for 30 min and filtered. The precipitate was washed with water, air-dried and crystallized from methanoldichloromethane to give the title compound (6.3 g): mp 294°-296° C.; ir (nujol mull) 3300, 3180, 1650, 1625, 1598 and 1560 cm-1 ; uv max (MeOH) 251 nm (ε=63670); nmr (DMSO-d6) δ 3.85 (m, 14H) and 7.4 (m, 7H); and Anal. Calcd for C22H23N7O2 : C, 63.29% H, 5.55% N, 23.49% and Found: C, 62.96% H, 5.60% N, 23.61%.

Workup

  1. temperatureThe mixture was refluxed for 18 hr
  2. customThe resulting precipitate was collected on a filter
  3. customThe filtrate was evaporated to dryness
  4. additionA suspension of the precipitate
  5. stirringthe evaporated filtrate in a cold, aqueous solution of sodium bicarbonate (5% w/v) was stirred for 30 min
  6. filtrationfiltered
  7. washThe precipitate was washed with water
  8. customair-dried
  9. customcrystallized from methanoldichloromethane

Sources & evidence

ORD record
ord-4260806d8cd64f0c97e65a3dd313b2a5
Source dataset
uspto-grants-1982_09
Patent number
US04351832

Reaction notes

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