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 985101Notes

Reaction equation

HRID 985101 reaction equation
[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]

Participants

3

Reactant 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

Product 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

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-738e1fb30b3045f2a673d4b278cd6fc3
Source dataset
uspto-grants-2005_03
Patent number
US06869949B2

Reaction notes

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