Tetrahydrofuran → HCID 70509913, compound

HRID 2295743Notes

Reaction equation

HRID 2295743 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:33][C:34]([Cl:36])=[O:35])[CH2:32][CH2:31][CH2:30][CH2:29][CH2:28]1>C(N(CC)CC)C>[OH2:1].[ClH:36].[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:34](=[O:35])[CH:33]=[C:27]3[CH2:32][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 12682124Cyclohexylideneacetyl chloride

Product 1

HCID 70509913HCID 70509913, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To 20 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 0.63 g of cyclohexylideneacetyl chloride, after which the mixture was stirred at room temperature for 8 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 1.05 g of the desired Compound No. 31 hydrochloride hydrate in the form of colourless powdery crystals melting at 210°-212° C. (with decomposition).

Workup

  1. stirringafter which the mixture was stirred at room temperature for 8 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-7d6ab772cd564ac29dca38e61b18c410
Source dataset
uspto-grants-1984_01
Patent number
US04426382

Reaction notes

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