Borane → (R)-2-chloro-5-((1-(3-chlorophenyl)ethylamino)methyl)benzenesulfonamide

HRID 1801578Notes

Reaction equation

HRID 1801578 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[C:7]([CH:20]=[CH:21][C:22]=1[Cl:23])[C:8]([NH:10][C@@H:11]([C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=1)[CH3:12])=O)(=[O:4])=[O:3].B>C1COCC1>[Cl:23][C:22]1[CH:21]=[CH:20][C:7]([CH2:8][NH:10][C@@H:11]([C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([Cl:19])[CH:14]=2)[CH3:12])=[CH:6][C:5]=1[S:2]([NH2:1])(=[O:3])=[O:4]

Participants

4

Reactant 2

HCID 6331BoraneHCID 91647343-(aminosulfonyl)-4-chloro-N-((1R)-1-(3-chlorophenyl)ethyl)benzamide

Product 1

HCID 24953406(R)-2-chloro-5-((1-(3-chlorophenyl)ethylamino)methyl)benzenesulfonamideYield 39.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(aminosulfonyl)-4-chloro-N-((1R)-1-(3-chlorophenyl)ethyl)benzamide 38 (0.558 g, 1.49 mmol) in THF (10 mL) at room temperature was added borane (0.138 g, 9.97 mmol) (10 mL, 1 M in THF). The reaction mixture was heated to reflux for 24 h, quenched with 1 M NaOH, and diluted with EtOAc. The organic phase was washed with water (1×), brine (1×), dried over MgSO4, filtered, and concentrated in vacuo. Purification by flash column chromatography on silica gel (eluted with 40% to 80% EtOAc in hexanes) gave (R)-2-chloro-5-((1-(3-chlorophenyl)ethylamino)methyl)benzenesulfonamide 39 (0.210 g, 39.1% yield) as a white solid. 1H NMR (400 MHz, CDCl3) δ 1.36 (d, J=6.5 Hz, 3H), 3.64 (s, 2H), 3.76 (q, J=6.6 Hz, 1H), 5.20 (s br, 2H), 7.19-7.31 (m, 5H), 7.44-7.46 (m, 2H), 8.01 (s, 1H). Mass spectrum: calculated for C15H16Cl2N2O2S 358.0. found 359.1 (M++1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 24 h
  3. customquenched with 1 M NaOH
  4. additiondiluted with EtOAc
  5. washThe organic phase was washed with water (1×), brine (1×)
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by flash column chromatography on silica gel (eluted with 40% to 80% EtOAc in hexanes)

Sources & evidence

ORD record
ord-eda849523189418a89cd30fadf957297
Source dataset
uspto-grants-2013_01
Patent number
US08349831B2

Reaction notes

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