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

HRID 1883067Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1883067
[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

Komponenten

8

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d923b595058b4f38a5f24aae5c79b264
Quelldatensatz
uspto-grants-2004_07
Patentnummer
US06759414B2

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