Water → 7-(2,4-Dichlorophenyl)-2-[1-(1-methylethyl)piperidin-4-yl][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 2088673

Reaktionsgleichung

Reaktionsgleichung von HRID 2088673
[Cl-].[Ca+2].[Cl-].C([O:6][C:7](=O)[NH:8][C:9]([C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][C:14]=1[Cl:20])=[CH:10][C:11]#[N:12])C.[CH3:22][CH:23]([N:25]1[CH2:30][CH2:29][CH:28]([C:31]([NH:33][NH2:34])=O)[CH2:27][CH2:26]1)[CH3:24].O>CN1CCCC1=O>[Cl:20][C:14]1[CH:15]=[C:16]([Cl:19])[CH:17]=[CH:18][C:13]=1[C:9]1[NH:8][C:7](=[O:6])[N:34]2[N:33]=[C:31]([CH:28]3[CH2:29][CH2:30][N:25]([CH:23]([CH3:24])[CH3:22])[CH2:26][CH2:27]3)[N:12]=[C:11]2[CH:10]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 5284359Calcium ChlorideHCID 583059791-(Propan-2-yl)piperidine-4-carbohydrazideHCID 76754608Ethyl[2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate

Produkt 1

HCID 1361041847-(2,4-Dichlorophenyl)-2-[1-(1-methylethyl)piperidin-4-yl][1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
160 °C

Versuchsvorschrift

In a round-bottom flask fitted with reflux condenser and a drying tube filled with calcium chloride, 500 mg (1.70 mmol) of ethyl[2-cyano-1-(2,4-dichlorophenyl)ethenyl]carbamate and 310 mg (1.70 mmol) of 1-(1-methylethyl)piperidin-4-carbohydrazide (Example 38A) were dissolved in 2 ml of 1-methyl-2-pyrrolidone, and the reaction mixture was stirred at 160° C. for 3 h. The reaction solution was cooled to 100° C., water (20 ml) was added and the mixture was then cooled to RT and stirred for 15 min. The reaction mixture was extracted with dichloromethane (3×50 ml), and the combined organic phases were dried over magnesium sulfate and concentrated. The crude product was chromatographed on basic aluminum oxide (mobile phase dichloromethane/methanol 10:1, then dichloromethane/methanol/17% strength aqueous ammonia solution 15:2:0.2). This gave 2.55 g (78% of theory) of the product.

Aufarbeitung

  1. customIn a round-bottom flask fitted
  2. temperaturewith reflux condenser and a drying tube
  3. temperatureThe reaction solution was cooled to 100° C.
  4. temperaturethe mixture was then cooled to RT
  5. stirringstirred for 15 min
  6. extractionThe reaction mixture was extracted with dichloromethane (3×50 ml)
  7. dry with materialthe combined organic phases were dried over magnesium sulfate
  8. concentrationconcentrated
  9. customThe crude product was chromatographed on basic aluminum oxide (mobile phase dichloromethane/methanol 10:1

Quellen und Nachweise

ORD-Eintrag
ord-5232c86f91d94bf9aef12e40250028c5
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436003B2

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