Borane;tetrahydrofuran → HCID 68915595, compound

HRID 870355Notes

Reaction equation

HRID 870355 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]=[N:16][C:17]3[CH2:18][CH:19]([NH:24][C:25](=O)[CH2:26][CH3:27])[CH2:20][CH2:21][C:22]=3[CH:23]=2)(=[O:12])=[O:11])=[CH:6][CH:5]=1.B.C1COCC1>C1COCC1>[CH2:25]([NH:24][CH:19]1[CH2:18][C:17]2[N:16]=[CH:15][C:14]([NH:13][S:10]([C:7]3[CH:6]=[CH:5][C:4]([O:3][C:2]([F:30])([F:29])[F:1])=[CH:9][CH:8]=3)(=[O:12])=[O:11])=[CH:23][C:22]=2[CH2:21][CH2:20]1)[CH2:26][CH3:27]

Participants

4

Reactant 2

HCID 2723981Borane;tetrahydrofuranHCID 68912306HCID 68912306, compound

Product 1

HCID 68915595HCID 68915595, compoundYield 64.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-[3-(4-trifluoromethoxy-benzenesulfonylamino)-5,6,7,8-tetrahydroquinolin-7-yl]-propionamide (260 mg, 0.58 mmol) in THF (10 ml) was added dropwise 1M BH3.THF (5.8 ml) and the mixture was stirred at room temperature for 6 h. It was then quenched by careful addition of 1N aqueous HCl (10 ml) and the resulting solution was heated at reflux for 4 h. The solution was next cooled to room temperature, 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:MeOH, 95:5) to give the title compound (160 mg, 64%) as a white solid.

Workup

  1. customIt was then quenched by careful addition of 1N aqueous HCl (10 ml)
  2. temperaturethe resulting solution was heated
  3. temperatureat reflux for 4 h
  4. temperaturenext cooled to room temperature
  5. additiondiluted with CH2Cl2
  6. customSeparation of the layers
  7. customdrying
  8. custom(Na2SO4) of the organic phase and evaporation in vacuo
  9. customprovided the crude material, which
  10. customwas purified by flash column chromatography (CH2Cl2:MeOH, 95:5)

Sources & evidence

ORD record
ord-a8e48e16fb3544b3945dcbb1bbd0227a
Source dataset
uspto-grants-2015_03
Patent number
US08969552B2

Reaction notes

Loading…