Pyridine → N-(6-Nitro-1-oxo-indan-5-yl)-3-cyclopentyl-propionamide

HRID 2422827Notes

Reaction equation

HRID 2422827 reaction equation
N1C=CC=CC=1.[NH2:7][C:8]1[CH:9]=[C:10]2[C:14](=[CH:15][C:16]=1[N+:17]([O-:19])=[O:18])[C:13](=[O:20])[CH2:12][CH2:11]2.[CH:21]1([CH2:26][CH2:27][C:28](Cl)=[O:29])[CH2:25][CH2:24][CH2:23][CH2:22]1>ClC(Cl)C>[N+:17]([C:16]1[CH:15]=[C:14]2[C:10]([CH2:11][CH2:12][C:13]2=[O:20])=[CH:9][C:8]=1[NH:7][C:28](=[O:29])[CH2:27][CH2:26][CH:21]1[CH2:25][CH2:24][CH2:23][CH2:22]1)([O-:19])=[O:18]

Participants

5

Reactant 3

HCID 1049PyridineHCID 660393-Cyclopentylpropionyl chlorideHCID 150841165-Amino-6-nitro-1-indanone

Product 1

HCID 59745250N-(6-Nitro-1-oxo-indan-5-yl)-3-cyclopentyl-propionamideYield 83%

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

Pyridine (0.1 g, 1.3 mmol) was added to a suspension of 5-amino-6-nitro-indan-1-one (0.19 g, 1 mmol) in 15 ml of anhydrous dichloroethane followed by the addition of 3-cyclopentylpropionyl chloride (0.193 mg, 1.2 mmol) at room temperature under argon. The mixture was stirred at room temperature for 24 hours. The solvent was removed under reduced pressure and the residue was purified by column (hexane/EtOAc, 5:1) to give a yellow solid (0.26 g, 83%). 1H-NMR (DMSO-d6): δ 10.47 (s, 1H, NH, exchangeable with D2O), 8.06 (s, 1H), 7.87 (s, 1H), 3.15 (m, 2H), 2.69 (m, 2H), 2.38 (t, 2H, J=7.8 Hz), 1.74 (m, 2H), 1.59-1.46 (m, 7H), 1.08 (m, 2H). MS: 317 (M+1).

Workup

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

Sources & evidence

ORD record
ord-6f0f5d31319d46909545f943365ca58b
Source dataset
uspto-grants-2011_06
Patent number
US07960436B2

Reaction notes

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