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

HRID 988719ノート

反応式

HRID 988719 の反応式
[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

参加物

8

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 1049Pyridine溶媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-903c31855b404beaacb1f861b75fe92a
出典データセット
uspto-grants-2003_10
特許番号
US06635657B1

反応ノート

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