Dimethylformamide → 6-[4-(6,7-dimethoxyquinazolin-4-yl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone

HRID 704633

Reaction equation

HRID 704633 reaction equation
[N:1]1([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:6][CH2:5][NH:4][CH2:3][CH2:2]1.Cl.Cl[C:20]1[C:29]2[C:24](=[CH:25][C:26]([O:32][CH3:33])=[C:27]([O:30][CH3:31])[CH:28]=2)[N:23]=[CH:22][N:21]=1.CN(C)C=O>C(N(CC)CC)C>[CH3:31][O:30][C:27]1[CH:28]=[C:29]2[C:24](=[CH:25][C:26]=1[O:32][CH3:33])[N:23]=[CH:22][N:21]=[C:20]2[N:4]1[CH2:5][CH2:6][N:1]([C:7]2[CH:8]=[C:9]3[C:14](=[CH:15][CH:16]=2)[NH:13][C:12](=[O:17])[CH2:11][CH2:10]3)[CH2:2][CH2:3]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 111178966-(piperazin-1-yl)-3,4-dihydroquinolin-2(1H)-oneHCID 220221614-Chloro-6,7-dimethoxyquinazoline hydrochloride

Product 1

HCID 200728786-[4-(6,7-dimethoxyquinazolin-4-yl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinoneYield 34.8%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a mixture of 6-(1-piperazinyl)-3,4-dihydro-2(1H)-quinolinone (1.28 g), 4-chloro-6,7-dimethoxyquinazoline hydrochloride (1.43 g) and N,N-dimethylformamide (50 ml) was added triethylamine (560 mg) and the mixture was stirred for 8 hours at ambient temperature. The solvent was removed under reduced pressure and to the obtained residue were added water (20 ml), tetrahydrofuran (10 ml) and ethyl acetate (10 ml). The separated organic layer was washed with brine, dried over magnesium sulfate and concentrated. The residue was subjected to a column chromatography on silica gel (80 g) and eluted with 10% solution of methanol in chloroform. The fractions containing the object compound were combined and concentrated. The obtained residue was subjected to a column chromatography on alumina (60 g) and eluted with 5% solution of methanol in chloroform. The fractions containing the object compound were combined and concentrated to give 6-[4-(6,7-dimethoxyquinazolin-4-yl)-1-piperazinyl]-3,4-dihydro-2(1H)-quinolinone (0.8 g).

Workup

  1. customThe solvent was removed under reduced pressure and to the obtained residue
  2. additionwere added water (20 ml), tetrahydrofuran (10 ml) and ethyl acetate (10 ml)
  3. washThe separated organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. washeluted with 10% solution of methanol in chloroform
  7. additionThe fractions containing the object compound
  8. concentrationconcentrated
  9. washeluted with 5% solution of methanol in chloroform
  10. additionThe fractions containing the object compound
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-5393d9cbede54d68b2901fb6b56204a5
Source dataset
uspto-grants-1991_01
Patent number
US04988698

Linked notes

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