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

HRID 2196860노트

반응식

HRID 2196860 반응식
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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 63651,1-Dichloroethane용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-5b2e91ef23994068ba4fe0e8211635db
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338487B2

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