Ammonium Chloride → (7R,8R,9R)-2,3,7-trimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

HRID 895599Notes

Reaction equation

HRID 895599 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@@H:10]([OH:20])[C:9](=[O:21])[C:8]=3[CH:7]=[CH:6][N:5]2[C:22]=1[CH3:23].[CH3:24][Li].[Cl-].[NH4+]>O1CCCC1>[CH3:1][C:2]1[N:3]=[C:4]2[C:13]3[NH:12][C@H:11]([C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)[C@@H:10]([OH:20])[C@:9]([CH3:24])([OH:21])[C:8]=3[CH:7]=[CH:6][N:5]2[C:22]=1[CH3:23]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59943673(8R,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-oneHCID 178418348HCID 178418348, compound

Product 1

HCID 10286525(7R,8R,9R)-2,3,7-trimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3.5 g of (8R,9R)-2,3-dimethyl-8-hydroxy-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one are suspended in 70 ml of tetrahydrofuran under argon and treated dropwise at −50° C. with a solution of methyllithium (1.6M solution in diethyl ether). The temperature is then allowed to rise to room temperature, and the mixture is poured into a saturated aqueous ammonium chloride solution and extracted three times with 100 ml of dichloromethane each time. The combined organic phases are washed with a little water, dried over sodium sulfate and concentrated to dryness in vacuo. The oily residue obtained is chromatographed on silica gel (eluent: dichloromethane/methanol 13/1). 1.66 g of the title compound are obtained as colorless crystals of melting point 137-8° C. (diethyl ether).

Workup

  1. customto rise to room temperature
  2. extractionextracted three times with 100 ml of dichloromethane each time
  3. washThe combined organic phases are washed with a little water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated to dryness in vacuo
  6. customThe oily residue obtained
  7. customis chromatographed on silica gel (eluent: dichloromethane/methanol 13/1)

Sources & evidence

ORD record
ord-b2c7e1cf639b4c64a3dce8cc4fcf1fb0
Source dataset
uspto-grants-2005_07
Patent number
US06916825B2

Reaction notes

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