Water → HCID 10155056, compound

HRID 1934371Notes

Reaction equation

HRID 1934371 reaction equation
[S:1](=O)(=O)(O)O.O[C@@H:7]1[C:16]2[CH:15]=[CH:14][N:13]3[C:17]([CH3:21])=[C:18]([CH3:20])[N:19]=[C:12]3[C:11]=2[NH:10][C@H:9]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C@H:8]1[OH:28].O.[OH-].[Na+].O1[CH2:37][CH2:36]OCC1>C(SCC)C>[CH3:20][C:18]1[N:19]=[C:12]2[C:11]3[NH:10][C@H:9]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[C@@H:8]([OH:28])[C@H:7]([S:1][CH2:36][CH3:37])[C:16]=3[CH:15]=[CH:14][N:13]2[C:17]=1[CH3:21]

Participants

7

Reactant 5

HCID 962WaterHCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 312751,4-DioxaneHCID 10215014(7R,8R,9R)-2,3-dimethyl-7,8-dihydroxy-9-phenyl-7,8,9,10-tetrahydro-imidazo[1,2-h][1,7]naphthyridine

Product 1

HCID 10155056HCID 10155056, compound

Reagents, catalysts & solvents 1

HCID 9609Ethyl sulfideSolvent

Procedure

1.9 g of concentrated sulphuric acid are added slowly at room temperature with stirring to 3 g of (7R,8R,9R)-7,8-dihydroxy-2,3-dimethyl-9-phenyl-7,8,9,10-tetra-hydroimidazo[1,2-h][1,7]naphthyridine, dissolved in a mixture of 40 ml of dry dioxan and 4 ml of ethylsulfide: The temperature is brought to 50° C. by external heating and is then kept for 15 min. After cooling to room temperature, the mixture is poured into 300 g of a mixture of crushed ice and water. The pH is adjusted to neutral by adding aqueous 2N sodium hydroxide solution. The mixture is extracted three times (50 ml each) with ethyl acetate, the organic layers are collectively washed with water and dried over potassium carbonate. The solvent is stripped off under reduced pressure and the solid residue that remains is purified by chromatography on silica gel (mobile phase: diethyl ether). 700 mg of the title compound of m.p. 220-223° C. are obtained after crystallisation from 2-propanol.

Workup

  1. customis brought to 50° C.
  2. temperatureby external heating
  3. extractionThe mixture is extracted three times (50 ml each) with ethyl acetate
  4. washthe organic layers are collectively washed with water
  5. dry with materialdried over potassium carbonate
  6. customthe solid residue that remains is purified by chromatography on silica gel (mobile phase: diethyl ether)

Sources & evidence

ORD record
ord-72eae5d82c9644b4ae56e90722ce9285
Source dataset
uspto-grants-2002_05
Patent number
US06384048B1

Reaction notes

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