Tetrahydrofuran → HCID 70509013, compound

HRID 2295742Notes

Reaction equation

HRID 2295742 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.[O:27]([CH2:34][C:35]([Cl:37])=[O:36])[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>C(N(CC)CC)C>[OH2:1].[ClH:37].[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:35](=[O:36])[CH2:34][O:27][C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[CH2:23][CH2:22]2)[N:8]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 69703Phenoxyacetyl chlorideHCID 6162672-(1-Piperazinyl)-4-amino-6,7-dimethoxyquinazoline

Product 1

HCID 70509013HCID 70509013, 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. There was then added to the resulting mixture 0.7 g of phenoxyacetyl chloride, and the mixture was stirred at room temperature for 4 hours. The reaction mixture was then concentrated by evaporation under reduced pressure, and the residue was extracted with chloroform. The extract was washed with water, and then the solvent was distilled from the extract under reduced pressure. The resulting residue was dissolved in ethanol, and a 10% w/w solution of hydrogen chloride in ethanol was added to this solution. The crystals thereby produced were collected by filtration and dried, to give 1.04 g of the desired Compound No. 27 hydrochloride hydrate in the form of pale yellow powdery crystals melting at 238°-240° C. (with decomposition).

Workup

  1. concentrationThe reaction mixture was then concentrated by evaporation under reduced pressure
  2. extractionthe residue was extracted with chloroform
  3. washThe extract was washed with water
  4. distillationthe solvent was distilled from the
  5. extractionextract under reduced pressure
  6. dissolutionThe resulting residue was dissolved in ethanol
  7. additiona 10% w/w solution of hydrogen chloride in ethanol was added to this solution
  8. customThe crystals thereby produced
  9. filtrationwere collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-5656a9b1866e4b1693242e67deef6a11
Source dataset
uspto-grants-1984_01
Patent number
US04426382

Reaction notes

Loading…