Borane;tetrahydrofuran → N-(3-Propylamino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl)-4-trifluoromethoxybenzenesulfonamide

HRID 870373

반응식

HRID 870373 반응식
[F:1][C:2]([F:30])([F:29])[O:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH:13][C:14]2[CH:15]=[C:16]3[O:23][CH2:22][CH:21]([NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:20][C:17]3=[N:18][CH:19]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.B.C1COCC1>C1COCC1>[CH2:25]([NH:24][CH:21]1[CH2:22][O:23][C:16]2[C:17](=[N:18][CH:19]=[C:14]([NH:13][S:10]([C:7]3[CH:8]=[CH:9][C:4]([O:3][C:2]([F:29])([F:1])[F:30])=[CH:5][CH:6]=3)(=[O:12])=[O:11])[CH:15]=2)[CH2:20]1)[CH2:26][CH3:27]

참가 물질

4

반응물 2

HCID 2723981Borane;tetrahydrofuranHCID 68914768N-[7-(4-Trifluoromethoxy-benzenesulfonylamino)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl]-propionamide

생성물 1

HCID 68914481N-(3-Propylamino-3,4-dihydro-2H-pyrano[3,2-b]pyridin-7-yl)-4-trifluoromethoxybenzenesulfonamide수율 81.1%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-[7-(4-trifluoromethoxy-benzenesulfonylamino)-3,4-dihydro-2H-pyrano[3,2-b]pyridin-3-yl]-propionamide (93 mg, 0.20 mmol) in THF (20 ml) was added dropwise 1M BH3.THF (2.08 ml, 2.08 mmol) and the mixture was stirred at room temperature for 12 h. It was then quenched by adding carefully 1N aqueous HCl (8 ml) and then the resulting solution was heated at reflux for 4 h. The solution was cooled to room temperature, the aqueous mixture was adjusted to pH˜8 with 2 N NaOH solution and diluted with CH2Cl2. Separation of the layers, drying (Na2SO4) of the organic phase and evaporation in vacuo provided the crude material, which was purified by flash column chromatography (CH2Cl2:methanol, 97:3) to give the title compound (70 mg, 78%) as a white amorphous solid.

후처리

  1. customIt was then quenched
  2. additionby adding carefully 1N aqueous HCl (8 ml)
  3. temperaturethe resulting solution was heated
  4. temperatureat reflux for 4 h
  5. temperatureThe solution was cooled to room temperature
  6. additiondiluted with CH2Cl2
  7. customSeparation of the layers
  8. customdrying
  9. custom(Na2SO4) of the organic phase and evaporation in vacuo
  10. customprovided the crude material, which
  11. customwas purified by flash column chromatography (CH2Cl2:methanol, 97:3)

출처 및 근거

ORD 기록
ord-a26331a2bdbb4915ae4ebf5a28eb4a80
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08969552B2

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