Reaction #710567

Reaction equation

N-(cis-4-(2,4-Dimethoxybenzylamino)cyclohexyl)-2′,4′-difluorobiphenyl-4-sulfonamide

water

→

title compound

Yield 25.0%

N-(cis-4-Aminocyclohexyl)-2′,4′-difluorobiphenyl-4-sulfonamide

Yield 25.0%

Solvents

acetonitrile

EtOAc

Conditions

Workup

1. 1
   Washwashed with water (2×5 mL)
2. 2
   ExtractionThe washings were extracted with EtOAc (5 mL)
3. 3
   Dryingthe combined organics were dried over MgSO4
4. 4
   OtherAfter evaporation of the solvents
5. 5
   Washeluted with MeOH
6. 6
   OtherThe resulting material was further purified by chromatography (2 g Isolute II cartridge)
7. 7
   Washeluting with 0-10% 2 M NH3/MeOH in DCM

Procedure

N-(cis-4-(2,4-Dimethoxybenzylamino)cyclohexyl)-2′,4′-difluorobiphenyl-4-sulfonamide (see ABD787a) (52 mg, 0.10 mmol) was stirred in acetonitrile (3 mL) and water (1 mL) and ceric ammonium nitrate (144 mg, 0.26 mmol) was added. The mixture was stirred at 50° C. overnight and then diluted with EtOAc (15 mL) and washed with water (2×5 mL). The washings were extracted with EtOAc (5 mL) and the combined organics were dried over MgSO4. After evaporation of the solvents, the residue was loaded onto a 1 g SCX column and eluted with MeOH and then 20% 2 M NH3/MeOH in DCM. The resulting material was further purified by chromatography (2 g Isolute II cartridge), eluting with 0-10% 2 M NH3/MeOH in DCM to afford the title compound as an off-white powder (9 mg, 25%). 1H NMR (300 MHz, DMSO-d6): δ 0.86-0.98 (2H, m), 1.09-1.26 (2H, m), 1.55-1.68 (4H, m), 2.40 (1H, br s), 2.87 (1H, br s), 4.12 (1H, br s), 7.22 (1H, td, J=8 Hz, 2 Hz), 7.40 (1H, td, J=10 Hz, 2.5 Hz), 7.65 (1H, q, J=7 Hz), 7.71 (2H, d, J=9 Hz) and 7.85 (2H, d, J=9 Hz). LCMS: (MH)+=367.

Source