Triethylamine → 1-(2-Nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propan-1-one

HRID 593023Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 593023
[N+:1]([C:4]1[CH:15]=[C:7]2[CH2:8][N:9]([C:12](=[O:14])[CH3:13])[CH2:10][CH2:11][N:6]2[N:5]=1)([O-:3])=[O:2].[CH3:16]CN(CC)CC.C(Cl)(=O)CC>ClCCl>[N+:1]([C:4]1[CH:15]=[C:7]2[CH2:8][N:9]([C:12](=[O:14])[CH2:13][CH3:16])[CH2:10][CH2:11][N:6]2[N:5]=1)([O-:3])=[O:2]

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 62324Propionyl chlorideHCID 580439581-(2-Nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)ethanone

Produkt 1

HCID 866845021-(2-Nitro-6,7-dihydropyrazolo[1,5-a]pyrazin-5(4H)-yl)propan-1-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 2-nitro-4,5,6,7-tetrahydropyrazolo[1,5-a]pyrazine 209a (200 mg, 1.19 mmol) in dichloromethane (8 mL) was added Et3N (240 mg, 2.38 mmol). After stirring for 5 minutes, a solution of propionyl chloride (121 mg, 1.31 mmol) in dichloromethane (2 mL) was added and the reaction mixture was stirred at room temperature for 1 h. Analysis of the reaction mixture by LCMS showed complete conversion to the desired product. The mixture was washed with water and brine, dried over Na2SO4, and filtered. The filtrate was concentrated under reduced pressure to afford 265a (260 mg, 98%) as white solid, which was used in the next step without further purification. MS-ESI: [M+H]+ 225.0

Aufarbeitung

  1. stirringthe reaction mixture was stirred at room temperature for 1 h

Quellen und Nachweise

ORD-Eintrag
ord-4d49fcd841a54d2fb31d1f3fbc6f790a
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09238655B2

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