Acetic Acid → 2-(1-Cyclopropylpiperidin-4-yl)-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

HRID 2088678Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2088678
Cl.[Cl:2][C:3]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:4]=1[C:10]1[NH:15][C:14](=[O:16])[N:13]2[N:17]=[C:18]([CH:20]3[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]3)[N:19]=[C:12]2[CH:11]=1.C(O)(=O)C.C(O[C:33]1(O[Si](C)(C)C)[CH2:35][CH2:34]1)C.[Na]>CO>[CH:33]1([N:23]2[CH2:24][CH2:25][CH:20]([C:18]3[N:19]=[C:12]4[N:13]([C:14](=[O:16])[NH:15][C:10]([C:4]5[CH:5]=[CH:6][C:7]([Cl:9])=[CH:8][C:3]=5[Cl:2])=[CH:11]4)[N:17]=3)[CH2:21][CH2:22]2)[CH2:35][CH2:34]1

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5360545SodiumHCID 1363378137-(2,4-Dichlorophenyl)-2-(piperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one hydrochloride

Produkt 1

HCID 1361041872-(1-Cyclopropylpiperidin-4-yl)-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1.00 g (2.50 mmol) of 7-(2,4-dichlorophenyl)-2-(piperidin-4-yl)[1,2,4]triazolo[1,5-c]pyrimidin-5(6H)-one hydrochloride and 3 Å molecular sieve (1 g) were initially charged in 15 ml of dry methanol and acetic acid (1.43 ml, 25 mmol) of 3.01 ml (2.61 g, 15 mmol) of [(1-ethoxy-1-cyclopropyl)oxy]-trimethylsilane and 690 mg (11 mmol) of sodium cyanoborhydride were then added. The mixture was stirred at reflux overnight. The mixture was cooled to RT and the reaction mixture was filtered. 50 ml of dichloromethane and 50 ml of water were added to the filtrate, and the mixture was extracted. The organic phase was dried over magnesium sulfate and concentrated on a rotary evaporator. This gave 540 mg (53% of theory) of the product.

Aufarbeitung

  1. temperatureat reflux overnight
  2. filtrationthe reaction mixture was filtered
  3. addition50 ml of dichloromethane and 50 ml of water were added to the filtrate
  4. extractionthe mixture was extracted
  5. dry with materialThe organic phase was dried over magnesium sulfate
  6. concentrationconcentrated on a rotary evaporator

Quellen und Nachweise

ORD-Eintrag
ord-36a955669ac54e33b1361bc8c9d835f4
Quelldatensatz
uspto-grants-2013_05
Patentnummer
US08436003B2

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