Water → HCID 10286449, compound

HRID 723379Notes

Reaction equation

HRID 723379 reaction equation
[OH:1][CH:2]1[C:11](=[O:12])[C:10]2[CH:9]=[CH:8][N:7]3[C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=[C:6]3[C:5]=2[NH:4][CH:3]1[C:18]1[CH:22]=[CH:21][S:20][CH:19]=1.[BH4-].[Na+].O.C(=O)([O-])O.[Na+]>CO.Cl>[OH:12][CH:11]1[C:10]2[CH:9]=[CH:8][N:7]3[C:13]([CH3:17])=[C:14]([CH3:16])[N:15]=[C:6]3[C:5]=2[NH:4][CH:3]([C:18]2[CH:22]=[CH:21][S:20][CH:19]=2)[CH:2]1[OH:1]

Participants

7

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 21873942HCID 21873942, compound

Product 1

HCID 10286449HCID 10286449, compoundYield 89.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 887MethanolSolvent

Procedure

50 mg of 8-hydroxy-2,3-dimethyl-9-(3-thienyl)-7,8,9,10-tetrahydroimidazo[1,2-h][1,7]naphthyridin-7-one are suspended in 5 ml of methanol and treated with 100 mg of sodium borohydride at room temperature with vigorous stirring. After stirring at room temperature for 1 hour, the solvent is stripped off in vacuo, the residue is covered with a layer of 5 ml of water, the mixture is adjusted to pH 1 with a few drops of semisaturated aqueous hydrochloric acid and then adjusted to pH 8 using saturated aqueous sodium hydrogen carbonate solution, extracted three times with 20 ml of methylene chloride each time, the combined organic phases are concentrated to dryness in vacuo and the remaining solid residue is purified on silica gel (eluent: methylene chloride/methanol=13/1). 45 mg of the title compound of m.p. 134–38° C. are obtained.

Workup

  1. extractionextracted three times with 20 ml of methylene chloride each time
  2. concentrationthe combined organic phases are concentrated to dryness in vacuo
  3. customthe remaining solid residue is purified on silica gel (eluent: methylene chloride/methanol=13/1)

Sources & evidence

ORD record
ord-561e6fb065d04ce6932b72ab152a01f8
Source dataset
uspto-grants-2006_11
Patent number
US07141567B2

Reaction notes

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