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

HRID 2196860ノート

反応式

HRID 2196860 の反応式
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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 63651,1-Dichloroethane溶媒

実験手順

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=7.8Hz), 1.74 (m, 2H), 1.59-1.46 (m, 7H), 1.08 (m, 2H). MS: 317 (M+1).

後処理

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

出典と根拠

ORDレコード
ord-5b2e91ef23994068ba4fe0e8211635db
出典データセット
uspto-grants-2012_12
特許番号
US08338487B2

反応ノート

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