HCID 59745253, compound → HCID 24990778, compound

HRID 2422834Notes

Reaction equation

HRID 2422834 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[C:7]([N+:23]([O-])=O)=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH:11]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:10][CH2:9]2)[CH3:2]>CO.[Ni]>[CH2:1]([O:3][C:4](=[O:26])[NH:5][C:6]1[C:7]([NH2:23])=[C:8]2[C:12](=[CH:13][CH:14]=1)[CH:11]([NH:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[CH2:10][CH2:9]2)[CH3:2]

Participants

4

Reactant 1

HCID 59745253HCID 59745253, compound

Product 1

HCID 24990778HCID 24990778, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A solution of [4-nitro-1-(4-fluoro-phenylamino)-indan-5-yl]-carbamic acid ethyl ester (200 mg) in 20 ml of methanol was added a catalytic amount of Raney Ni. 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. 1H-NMR (DMSO-d6): δ 8.51 (brs, 1H, NH, exchangeable with D2O), 6.94 (dd, 2H, J=9.0, 18.6 Hz), 6.88 (d, 1H, J=8.1 Hz), 6.66 (dd, 2H, J=4.2, 9.0 Hz), 6.49 (d, 1H, J=8.1 Hz), 5.70 (brs, 1H, NH, exchangeable with D2O), 4.80 (m, 3H, NH2 and CH)), 4.05 (q, 2H, J=7.2 Hz), 2.74 (ddd, 1H, J=3.6, 8.7, 15.6 Hz), 2.60-2.36 (m, 2H), 1.71 (m, 1H), 1.20 (t, 3H, J=7.2 Hz). MS: 330 (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

Sources & evidence

ORD record
ord-deb481ccfb7f4b85b540d9990b19ce6d
Source dataset
uspto-grants-2011_06
Patent number
US07960436B2

Reaction notes

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