Hydrochloric Acid → (8R,9R)-8-Hydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

HRID 723384Notes

Reaction equation

HRID 723384 reaction equation
Cl.[Si]([O:9][C@H:10]1[C:19](=[O:20])[C:18]2[CH:17]=[CH:16][N:15]3[CH:21]=[C:22]([CH3:24])[N:23]=[C:14]3[C:13]=2[NH:12][C@@H:11]1[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1)(C(C)(C)C)(C)C.[OH-].[Na+]>CO>[OH:9][C@H:10]1[C:19](=[O:20])[C:18]2[CH:17]=[CH:16][N:15]3[CH:21]=[C:22]([CH3:24])[N:23]=[C:14]3[C:13]=2[NH:12][C@@H:11]1[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 20767689(8R,9R)-8-(tert-butyldimethylsilanyloxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Product 1

HCID 69586463(8R,9R)-8-Hydroxy-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

30 ml of concentrated hydrochloric acid are added dropwise at room temperature in the course of 20 minutes to 29.8 g (73.1 mmol) of (8R,9R)-8-(tert-butyldimethylsilanyloxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one, dissolved in 30 ml of methanol. The mixture is stirred for a further 30 minutes at room temperature. The methanol is stripped off and the pH of the remaining solution is adjusted to 10 using 2M sodium hydroxide solution. The mixture is extracted three times with 30 ml of dichloromethane each time, the combined dichloromethane phases are washed once with 30 ml of water and the organic phase is dried over magnesium sulfate. The drying agent is filtered off, the filtrate is concentrated and the residue is brought to crystallization using diethyl ether. The crystallizate is filtered off with suction and dried in vacuo at 50° C. 12.2 g (57% of theory) of the title compound are obtained.

Workup

  1. extractionThe mixture is extracted three times with 30 ml of dichloromethane each time
  2. washthe combined dichloromethane phases are washed once with 30 ml of water
  3. dry with materialthe organic phase is dried over magnesium sulfate
  4. filtrationThe drying agent is filtered off
  5. concentrationthe filtrate is concentrated
  6. customthe residue is brought to crystallization
  7. filtrationThe crystallizate is filtered off with suction
  8. customdried in vacuo at 50° C

Sources & evidence

ORD record
ord-2bfd6333eacf4a1b865b366d79564ad9
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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