4-(Dimethylamino)-N-(2-fluoro-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenyl)benzamide → N-(3-(2-Amino-1-(6-morpholino-1H-indol-3-yl)ethyl)-2-fluorophenyl)-4-(dimethylamino)benzamide

HRID 2361354Notes

Reaction equation

HRID 2361354 reaction equation
[CH3:1][N:2]([CH3:39])[C:3]1[CH:38]=[CH:37][C:6]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([CH:16]([C:21]3[C:29]4[C:24](=[CH:25][C:26]([N:30]5[CH2:35][CH2:34][O:33][CH2:32][CH2:31]5)=[CH:27][CH:28]=4)[NH:23][CH:22]=3)[CH2:17][N+:18]([O-])=O)[C:11]=2[F:36])=[O:8])=[CH:5][CH:4]=1.[H][H]>CO.[Ni]>[NH2:18][CH2:17][CH:16]([C:12]1[C:11]([F:36])=[C:10]([NH:9][C:7](=[O:8])[C:6]2[CH:5]=[CH:4][C:3]([N:2]([CH3:1])[CH3:39])=[CH:38][CH:37]=2)[CH:15]=[CH:14][CH:13]=1)[C:21]1[C:29]2[C:24](=[CH:25][C:26]([N:30]3[CH2:35][CH2:34][O:33][CH2:32][CH2:31]3)=[CH:27][CH:28]=2)[NH:23][CH:22]=1

Participants

5

Reactant 2

HCID 679949194-(Dimethylamino)-N-(2-fluoro-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenyl)benzamideHCID 178418361HCID 178418361, compound

Product 1

HCID 67994859N-(3-(2-Amino-1-(6-morpholino-1H-indol-3-yl)ethyl)-2-fluorophenyl)-4-(dimethylamino)benzamideYield 82.1%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

A mixture of 4-(dimethylamino)-N-(2-fluoro-3-(1-(6-morpholino-1H-indol-3-yl)-2-nitroethyl)phenyl)benzamide (0.388 g, 0.730 mmol) and Raney Ni (a small amount) in MeOH (35 mL) was treated with hydrogen at 55 psi a Parr shaker apparatus for 3 hr. The catalyst was removed by suction filtration. The filtrate was concentrated under vacuum, diluted with CH2Cl2 (100 mL), washed with brine (25 mL) and dried over anhydrous MgSO4. Removal of solvent under vacuum provided the desired product (0.321 g, 0.599 mmol, 82% yield) as an off-white solid.

Workup

  1. customThe catalyst was removed by suction filtration
  2. concentrationThe filtrate was concentrated under vacuum
  3. additiondiluted with CH2Cl2 (100 mL)
  4. washwashed with brine (25 mL)
  5. dry with materialdried over anhydrous MgSO4
  6. customRemoval of solvent under vacuum

Sources & evidence

ORD record
ord-6beeff3ed10447f38b6f32c46ad9c983
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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