Water → HCID 10286449, 화합물

HRID 723379노트

반응식

HRID 723379 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

HCID 10286449HCID 10286449, 화합물수율 89.4%

시약·촉매·용매 2

HCID 313Hydrochloric Acid촉매HCID 887Methanol용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-561e6fb065d04ce6932b72ab152a01f8
출처 데이터셋
uspto-grants-2006_11
특허 번호
US07141567B2

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