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

HRID 870373

反応式

HRID 870373 の反応式
[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]

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-a26331a2bdbb4915ae4ebf5a28eb4a80
出典データセット
uspto-grants-2015_03
特許番号
US08969552B2

関連ノート

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