反応 #156757

反応方程式

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

water

→

title compound

収率 25.0%

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

収率 25.0%

溶媒

acetonitrile

EtOAc

反応条件

後処理

1. 1
   洗浄washed with water (2×5 mL)
2. 2
   抽出The washings were extracted with EtOAc (5 mL)
3. 3
   乾燥the combined organics were dried over MgSO4
4. 4
   その他After evaporation of the solvents
5. 5
   洗浄eluted with MeOH
6. 6
   その他The resulting material was further purified by chromatography (2 g Isolute II cartridge)
7. 7
   洗浄eluting with 0-10% 2 M NH3/MeOH in DCM

実験手順

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, 2.5Hz), 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.

出典