Triethylamine → Cyclohexane n-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]carboxamide

HRID 9408

반응식

HRID 9408 반응식
[N+:1]([C:4]1[CH:5]=[N:6][C:7]2[C:12]([C:13]=1[NH:14][CH2:15][C:16]([CH3:19])([NH2:18])[CH3:17])=[CH:11][CH:10]=[C:9]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[CH:8]=2)([O-:3])=[O:2].C(N(CC)CC)C.[CH:33]1([C:39](Cl)=[O:40])[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1>ClCCl>[CH3:17][C:16]([NH:18][CH:39]=[O:40])([CH3:19])[CH2:15][NH:14][C:13]1[C:12]2[C:7](=[CH:8][C:9]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[CH:10][CH:11]=2)[N:6]=[CH:5][C:4]=1[N+:1]([O-:3])=[O:2].[CH2:33]1[CH2:38][CH2:37][CH2:36][CH2:35][CH2:34]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 75938Cyclohexanecarbonyl chlorideHCID 86593761N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine

생성물 1

HCID 87586912Cyclohexane n-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]carboxamide수율 70%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

A solution of N1-(3-nitro-7-phenylquinolin-4-yl)-2-methylpropane-1,2-diamine (3.56 g, 10.6 mmol) in dichloromethane (100 mL) was cooled to 0° C. Triethylamine (3.0 mL, 21 mmol) and cyclohexanecarbonyl chloride (1.55 mL, 11.6 mmol) were sequentially added. The reaction was allowed to warm to ambient temperature and stirred for two hours. The reaction was washed sequentially with water (2×100 mL) and brine (100 mL), dried over sodium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by column chromatography on silica gel (eluting with 65:35 hexanes:ethyl acetate) to provide 3.33 g of cyclohexane N-[1,1-dimethyl-2-(3-nitro-7-phenylquinolin-4-ylamino)ethyl]carboxamide as a yellow solid.

후처리

  1. washThe reaction was washed sequentially with water (2×100 mL) and brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure
  5. customThe crude product was purified by column chromatography on silica gel (eluting with 65:35 hexanes:ethyl acetate)

출처 및 근거

ORD 기록
ord-f15ea28ffbee4c82a8f9b5a3dcec7661
출처 데이터셋
uspto-grants-2006_08
특허 번호
US07091214B2

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