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

HRID 870373Notes

Reaction equation

HRID 870373 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-a26331a2bdbb4915ae4ebf5a28eb4a80
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

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