Potassium Carbonate → (7R,8R,9R)-10-Acetyl-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h]-[1,7]naphthyridine

HRID 584845Notes

Reaction equation

HRID 584845 reaction equation
[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([OH:19])[C@H:6]([O:20]C(=O)C(C)(C)C)[C@H:5]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+]>CO>[C:1]([N:4]1[C:13]2[C:12]3=[N:14][C:15]([CH3:18])=[C:16]([CH3:17])[N:11]3[CH:10]=[CH:9][C:8]=2[C@@H:7]([OH:19])[C@H:6]([OH:20])[C@H:5]1[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 69263320(7R,8R,9R)-10-Acetyl-7-hydroxy-2,3-dimethyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine

Product 1

HCID 69288589(7R,8R,9R)-10-Acetyl-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetrahydroimidazo[1,2-h]-[1,7]naphthyridineYield 73%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

160 g of (7R,8R,9R)-10-acetyl-7-hydroxy-2,3-dimethyl-9-phenyl-8-pivaloyloxy-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridine are dissolved in 0.7 l of methanol with stirring and treated with 40 g of potassium carbonate. After approximately 10 min, the product begins to precipitate from the reaction mixture. After stirring for 1 h at room temperature, it is added to a solution of 200 g of ammonium chloride in 1.8 l of ice water. It is stirred for a further 1 h at ice-bath temperature, then the precipitated solid is filtered off with suction and washed with a little methanol (80 ml). After drying at 50° C. in a vacuum drying oven, 92.0 g (73%) of the title compound are isolated as a colorless solid of m.p. 260-261° C., which is used in the next stage without further purification. Alternatively, the tile compound can also be prepared according to examples 5 and 6.

Workup

  1. customto precipitate from the reaction mixture
  2. stirringAfter stirring for 1 h at room temperature
  3. additionit is added to a solution of 200 g of ammonium chloride in 1.8 l of ice water
  4. stirringIt is stirred for a further 1 h at ice-bath temperature
  5. filtrationthe precipitated solid is filtered off with suction
  6. washwashed with a little methanol (80 ml)
  7. customAfter drying at 50° C. in a vacuum
  8. customdrying oven

Sources & evidence

ORD record
ord-12ab2f13412d4eb49975c5b6e5926dab
Source dataset
uspto-grants-2005_08
Patent number
US06927292B2

Reaction notes

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