Tetrahydrofuran → HCID 70507736, compound

HRID 2295744Notes

Reaction equation

HRID 2295744 reaction equation
[O:1]1CCCC1.[NH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[C:9]([N:21]2[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]2)[N:8]=1.[C:27]1(=[CH:32][C:33]([Cl:35])=[O:34])[CH2:31][CH2:30][CH2:29][CH2:28]1>C(N(CC)CC)C>[OH2:1].[ClH:35].[NH2:6][C:7]1[C:16]2[C:11](=[CH:12][C:13]([O:19][CH3:20])=[C:14]([O:17][CH3:18])[CH:15]=2)[N:10]=[C:9]([N:21]2[CH2:26][CH2:25][N:24]([C:33](=[O:34])[CH:32]=[C:27]3[CH2:31][CH2:30][CH2:29][CH2:28]3)[CH2:23][CH2:22]2)[N:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazolineHCID 20473877HCID 20473877, compound

Product 1

HCID 70507736HCID 70507736, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 25 ml of tetrahydrofuran were added 1.16 g of 4-amino-6,7-dimethoxy-2-(1-piperazinyl)quinazoline and 1.5 g of triethylamine, after which the mixture was stirred for 30 minutes. To this mixture was then added 0.57 g of cyclopentylideneacetyl chloride, after which the mixture was stirred at room temperature for 15 hours. The reaction mixture was then concentrated by evaporation under reduced pressure and the residue was extracted with chloroform. After washing the extract with water, the solvent was distilled off and the residue was dissolved in ethanol. A 10% w/w solution of hydrogen chloride in ethanol was then added to this solution and the crystals thereby produced were collected by filtration, giving 0.60 g of the desired Compound No. 32 hydrochloride hydrate in the form of colourless powdery crystals melting at 238°-240° C. (with decomposition).

Workup

  1. stirringafter which the mixture was stirred at room temperature for 15 hours
  2. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  3. extractionthe residue was extracted with chloroform
  4. washAfter washing the
  5. extractionextract with water
  6. distillationthe solvent was distilled off
  7. dissolutionthe residue was dissolved in ethanol
  8. additionA 10% w/w solution of hydrogen chloride in ethanol was then added to this solution
  9. customthe crystals thereby produced
  10. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-b8ca939f98a64a4191d39724d8b314cd
Source dataset
uspto-grants-1984_01
Patent number
US04426382

Reaction notes

Loading…