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

HRID 2422828Notes

Reaction equation

HRID 2422828 reaction equation
[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][C:10]2=O)=[CH:6][C:5]=1[NH:14][C:15](=[O:23])[CH2:16][CH2:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)([O-:3])=[O:2].[F:24][C:25]([F:34])([F:33])[C:26]1[CH:32]=[CH:31][C:29]([NH2:30])=[CH:28][CH:27]=1.[B][B][B][B][B][B][B][B][B][B]>CO>[N+:1]([C:4]1[CH:12]=[C:11]2[C:7]([CH2:8][CH2:9][CH:10]2[NH:30][C:29]2[CH:31]=[CH:32][C:26]([C:25]([F:24])([F:33])[F:34])=[CH:27][CH:28]=2)=[CH:6][C:5]=1[NH:14][C:15](=[O:23])[CH2:16][CH2:17][CH:18]1[CH2:22][CH2:21][CH2:20][CH2:19]1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 99644-(Trifluoromethyl)anilineHCID 59745250N-(6-Nitro-1-oxo-indan-5-yl)-3-cyclopentyl-propionamideHCID 178419135HCID 178419135, compound

Product 1

HCID 67243576N-[6-Nitro-1-(4-trifluoromethyl-phenylamino)-indan-5-yl]-3-cyclopentyl-propionamideYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of N-(6-nitro-1-oxo-indan-5-yl)-3-cyclopentyl-propionamide (0.57 g, 1.8 mmol), 4-trifluoromethylaniline (0.35 g, 2.2 mmol), and decaborane (200 mg) in 20 ml of anhydrous methanol was stirred at room temperature overnight. The solvent was removed in vacuo and the residue was purified by column (hexane/EtOAc, 5:1) to give a pure product (0.65 g, 90%).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was purified by column (hexane/EtOAc, 5:1)

Sources & evidence

ORD record
ord-fb11f67975a84a29893190a945c5049d
Source dataset
uspto-grants-2011_06
Patent number
US07960436B2

Reaction notes

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