Acetone → (7R,8R,9R)-3-Bromo-8-hydroxy-7-(2-methoxyethoxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 985087Notes

Reaction equation

HRID 985087 reaction equation
C([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([Br:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([O:19][CH2:20][CH2:21][O:22][CH3:23])[C@H:6]([O:24]C(=O)C(C)(C)C)[C@H:5]1[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)(=O)C.[OH-].[K+].O.NN.CC(C)=O>CO>[Br:17][C:16]1[N:11]2[CH:10]=[CH:9][C:8]3[C@@H:7]([O:19][CH2:20][CH2:21][O:22][CH3:23])[C@H:6]([OH:24])[C@@H:5]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[NH:4][C:13]=3[C:12]2=[N:14][C:15]=1[CH3:18]

Participants

6

Reactant 4

HCID 180AcetoneHCID 14797Potassium HydroxideHCID 24654Hydrazine hydrate (1:1)HCID 69586421HCID 69586421, compound

Product 1

HCID 10310202(7R,8R,9R)-3-Bromo-8-hydroxy-7-(2-methoxyethoxy)-2-methyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridineYield 59%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
60 °C

Procedure

A suspension of 3.30 g (5.90 mmol) (7R,8R,9R)-10-acetyl-3-bromo-7-(2-methoxyethoxy)-2-methyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine, 1.00 ml (6.00 mmol) aqueous potassium hydroxide (6 N) and 2.00 ml (51.40 mmol) hydrazine hydrate in methanol is stirred at 60° C. for 4 h. The methanol is removed in vacuo and the reaction mixture is diluted with water. Subsequently the mixture is extracted twice with dichloromethane. The combined organic layers are washed with brine, dried over sodium sulphate and evaporated in vacuo. The crude product is purified by column chromatography (toluene/dioxane/acetic acid: 8/1/1) to give 1.50 g (3.47 mmol, 59%) of the title compound as a light yellow solid with a melting point of 153-154° C. (acetone).

Workup

  1. customThe methanol is removed in vacuo
  2. additionthe reaction mixture is diluted with water
  3. extractionSubsequently the mixture is extracted twice with dichloromethane
  4. washThe combined organic layers are washed with brine
  5. dry with materialdried over sodium sulphate
  6. customevaporated in vacuo
  7. customThe crude product is purified by column chromatography (toluene/dioxane/acetic acid: 8/1/1)

Sources & evidence

ORD record
ord-e0393ff0e4dc40a38453d6a03fd8b497
Source dataset
uspto-grants-2005_03
Patent number
US06869949B2

Reaction notes

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