2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → (8R,9R)-8-(tert-butyldimethylsilanyloxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 723400노트

반응식

HRID 723400 반응식
[Si:1]([O:8][C@H:9]1[C:18](=[O:19])[C:17]2[CH2:16][CH2:15][N:14]3[CH:20]=[C:21]([CH3:23])[N:22]=[C:13]3[C:12]=2[NH:11][C@@H:10]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>>[Si:1]([O:8][C@H:9]1[C:18](=[O:19])[C:17]2[CH:16]=[CH:15][N:14]3[CH:20]=[C:21]([CH3:23])[N:22]=[C:13]3[C:12]=2[NH:11][C@@H:10]1[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:3])[CH3:2]

참가 물질

3

반응물 2

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 69586123(8R,9R)-8-(tert-Butyldimethylsilanyloxy)-2-methyl-9-phenyl-5,6,7,8,9,10-hexahydro-imidazo[1,2-h][1,7]naphthyridin-7-one

생성물 1

HCID 20767689(8R,9R)-8-(tert-butyldimethylsilanyloxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

실험 절차

50.7 g (123.8 mmol) of (8R,9R)-8-(tert-butyldimethylsilanyloxy)-2-methyl-9-phenyl-5,6,7,8,9,10-hexahydroimidazo[1,2-h][1,7]naphthyridin-7-one are treated in portions at 5° C.–10° C. with 35.6 g (153.5 mmol) of 2,3-dichloro-5,6-dicyano-p-benzoquinone. After the end of the addition, the reaction mixture is stirred at room temperature for 2 days. The reaction mixture is extracted with 150 ml of sodium hydroxide solution and the sodium hydroxide solution phase separated off is extracted with 150 ml of toluene and the combined toluene phases are washed with 150 ml of water. The organic phase is concentrated and the residue is dried overnight in a high vacuum. The solid crystallised in this way is stirred in diisopropyl ether, filtered off with suction and dried in vacuo at 50° C. 10.1 g (20% of theory) of the title compound are obtained.

후처리

  1. additionAfter the end of the addition
  2. extractionThe reaction mixture is extracted with 150 ml of sodium hydroxide solution
  3. customthe sodium hydroxide solution phase separated off
  4. extractionis extracted with 150 ml of toluene
  5. washthe combined toluene phases are washed with 150 ml of water
  6. concentrationThe organic phase is concentrated
  7. customthe residue is dried overnight in a high vacuum
  8. customThe solid crystallised in this way
  9. stirringis stirred in diisopropyl ether
  10. filtrationfiltered off with suction
  11. customdried in vacuo at 50° C

출처 및 근거

ORD 기록
ord-70acbb3f825c4defb4582bac7283ea16
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141567B2

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