N-[6-Nitro-1-(4-trifluoromethyl-phenylamino)-indan-5-yl]-3-cyclopentyl-propionamide → N-[6-Amino-1-(4-trifluoromethyl-phenylamino)-indan-5-yl]-3-cyclopentyl-propionamide

HRID 2196862Notes

Reaction equation

HRID 2196862 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][CH:10]2[NH:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[CH:6][C:5]=1[NH:24][C:25](=[O:33])[CH2:26][CH2:27][CH:28]1[CH2:32][CH2:31][CH2:30][CH2:29]1)([O-])=O>CO.[Ni]>[NH2:1][C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][CH:10]2[NH:13][C:14]2[CH:15]=[CH:16][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:18][CH:19]=2)=[CH:6][C:5]=1[NH:24][C:25](=[O:33])[CH2:26][CH2:27][CH:28]1[CH2:29][CH2:30][CH2:31][CH2:32]1

Participants

4

Reactant 1

HCID 67243576N-[6-Nitro-1-(4-trifluoromethyl-phenylamino)-indan-5-yl]-3-cyclopentyl-propionamide

Product 1

HCID 24990779N-[6-Amino-1-(4-trifluoromethyl-phenylamino)-indan-5-yl]-3-cyclopentyl-propionamide

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

To a solution of N-[6-nitro-1-(4-trifluoromethyl-phenylamino)-indan-5-yl]-3-cyclopentyl-propionamide (200 mg) in 20 ml of methanol was added a catalytic amount of Raney Nickel. The resulting mixture was hydrogenated under regular pressure at room temperature for 4 hours. The reaction mixture was filtered through celite and washed with methanol. The filtrate was evaporated to dryness in vacuo and the residue was purified by column (hexane/EtOAc, 3:1) to give a white solid product in a quantitative yield. 1H-NMR (DMSO-d6): δ 9.01 (s, 1H, NH, exchangeable with D2O), 7.36 (d, 2H, J=8.4 Hz), 7.05 (s, 1H), 6.78 (d, 2H, J=8.4 Hz), 6.66 (d, 1H, NH, J=8.4 Hz, exchangeable with D2O), 6.31 (s, 1H), 4.88 (q, 1H, J=8.4 Hz), 4.69 (brs, 2H, NH2, exchangeable with D2O), 2.77 (ddd, 1H, J=15.3, 8.4, 3.6 Hz), 2.67 (m, 1H), 2.42 (m, 1H), 2.29 (t, 2H, J=7.5 Hz), 1.73 (m, 4H), 1.56 (m, 4H), 1.48 (m, 2H), 1.07 (m, 2H). MS: 432 (M+1).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. washwashed with methanol
  3. customThe filtrate was evaporated to dryness in vacuo
  4. customthe residue was purified by column (hexane/EtOAc, 3:1)
  5. customto give a white solid product in a quantitative yield

Sources & evidence

ORD record
ord-1ec6640398584c45892fed00be143f6b
Source dataset
uspto-grants-2012_12
Patent number
US08338487B2

Reaction notes

Loading…