Methanol → 3-(3-Chloro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diol

HRID 633835노트

반응식

HRID 633835 반응식
C[N+]1([O-])CC[O:5]CC1.[CH2:9]([C:12]1[C:13]([Cl:24])=[CH:14][N:15]=[C:16]2[C:21]=1[N:20]=[C:19]([O:22][CH3:23])[CH:18]=[CH:17]2)[CH:10]=C.[CH3:25][OH:26]>ClCCl.O.O.O.[Os](=O)(=O)=O.[K]>[Cl:24][C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:12]=1[CH2:9][CH:10]([OH:5])[CH2:25][OH:26])=[N:20][C:19]([O:22][CH3:23])=[CH:18][CH:17]=2

참가 물질

7

반응물 3

HCID 887MethanolHCID 82029Methyl morpholine oxideHCID 671828908-Allyl-7-chloro-2-methoxy-[1,5]naphthyridine

생성물 1

HCID 671805623-(3-Chloro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diol수율 96%

시약·촉매·용매 3

HCID 178526964HCID 178526964, 화합물촉매HCID 962Water용매HCID 6344Dichloromethane용매2회

실험 절차

N-Methylmorpholine-N-oxide (0.76 g, 64.0 mmol, 1.5 eq) is added at room temperature to a stirred solution of 8-allyl-7-chloro-2-methoxy-[1,5]naphthyridine (1.0 g, 4.26 mmol, 1.0 eq) in dichloromethane (40 mL) and water (4 mL), followed by potassium osmium(VI) oxide dihydrate (80 mg, 0.23 mmol, 0.05 eq). After 16 hours stirring at room temperature, the reaction mixture is extracted with dichloromethane (3×20 mL) and a saturated sodium sulfite aqueous solution (20 mL). The combined organic layers are washed with brine, dried over sodium sulfate, filtered and concentrated to give a crude product that is purified by column chromatography (silica gel, eluent: dichloromethane:methanol, 40:1, v/v) to afford 3-(3-chloro-6-methoxy-[1,5]naphthyridin-4-yl)-propane-1,2-diol as a light yellow solid (1.1 g, 96% yield).

후처리

  1. extractionthe reaction mixture is extracted with dichloromethane (3×20 mL)
  2. washThe combined organic layers are washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give a crude product that
  7. customis purified by column chromatography (silica gel, eluent

출처 및 근거

ORD 기록
ord-f9131a8b54c74f4980b72c37781675c1
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09321788B2

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