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

HRID 704633

반응식

HRID 704633 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8471Triethylamine용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-5393d9cbede54d68b2901fb6b56204a5
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04988698

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