Sodium Hydroxide → N-(5-Chloropyridin-2-yl)-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]-4-methoxycarbonylbenzamide

HRID 988719노트

반응식

HRID 988719 반응식
[CH:1]([N:4]1[CH2:9][CH2:8][CH:7]([C:10]([OH:12])=O)[CH2:6][CH2:5]1)([CH3:3])[CH3:2].S(Cl)(Cl)=O.[NH2:17][C:18]1[CH:33]=[C:32]([C:34]([O:36][CH3:37])=[O:35])[CH:31]=[CH:30][C:19]=1[C:20]([NH:22][C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][N:24]=1)=[O:21].[OH-].[Na+]>C(Cl)Cl.O.N1C=CC=CC=1>[Cl:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20](=[O:21])[C:19]2[CH:30]=[CH:31][C:32]([C:34]([O:36][CH3:37])=[O:35])=[CH:33][C:18]=2[NH:17][C:10]([CH:7]2[CH2:6][CH2:5][N:4]([CH:1]([CH3:2])[CH3:3])[CH2:9][CH2:8]2)=[O:12])=[N:24][CH:25]=1

참가 물질

8

반응물 4

HCID 14798Sodium HydroxideHCID 24386Thionyl ChlorideHCID 64841871-Isopropylpiperidine-4-Carboxylic AcidHCID 219063182-amino-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide

생성물 1

HCID 21906664N-(5-Chloropyridin-2-yl)-2-[(1-isopropylpiperidin-4-ylcarbonyl)amino]-4-methoxycarbonylbenzamide수율 52%

시약·촉매·용매 3

HCID 962Water용매HCID 1049Pyridine용매HCID 6344Dichloromethane용매

실험 절차

A solution of 1-isopropylpiperidine-4-carboxylic acid (2.0 g, 9.6 mmol) in methylene chloride (70 mL) was treated dropwise with thionyl chloride (0.70 mL, 9.6 mmol). After heating to reflux for 1 h, 2-amino-N-(5-chloropyridin-2-yl)-4-methoxycarbonylbenzamide (1.5 g, 4.8 mmol) was added. After 0.5 h, pyridine (0.80 mL) was added and the resulting mixture heated at reflux. After 12 h, the mixture was cooled, treated with water, 1 N NaOH (20 mL), and concentrated. The residue was purified by column chromatography (SiO2: 5% methanol:methylene chloride) affording 1.14 g (52%) of the title compound.

후처리

  1. temperatureAfter heating
  2. temperatureto reflux for 1 h
  3. temperaturethe resulting mixture heated
  4. temperatureat reflux
  5. waitAfter 12 h
  6. temperaturethe mixture was cooled
  7. concentrationconcentrated
  8. customThe residue was purified by column chromatography (SiO2: 5% methanol:methylene chloride)

출처 및 근거

ORD 기록
ord-903c31855b404beaacb1f861b75fe92a
출처 데이터셋
uspto-grants-2003_10
특허 번호
US06635657B1

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