Piperidine → HCID 178510024, Verbindung

HRID 2037015Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2037015
[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13]([CH:14]=O)=[C:9]3[N:8]=[C:7]([NH:16][C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)[CH:6]=2)[CH2:3][CH2:2]1.[NH:25]1[CH2:31][C:29](=[O:30])[NH:28][C:26]1=[O:27].N1CCCCC1>CCO>[CH:1]1([NH:4][C:5]2[N:10]3[N:11]=[CH:12][C:13](/[CH:14]=[C:31]4\[NH:25][C:26](=[O:27])[NH:28][C:29]\4=[O:30])=[C:9]3[N:8]=[C:7]([NH:16][C:17]3[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=3)[CH:6]=2)[CH2:2][CH2:3]1

Komponenten

5

Edukt 3

HCID 8082PiperidineHCID 10006HydantoinHCID 866546564-(7-(Cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile

Produkt 1

HCID 178510024HCID 178510024, VerbindungAusbeute 80 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

4-(7-(cyclopropylamino)-3-formylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile (75 mg, 0.24 mmol) was suspended in EtOH (2.4 mL). Hydantoin (36 mg, 0.35 mmol) and piperidine (36 μL, 0.35 mmol) were added and the reaction was heated to 80° C. After 15 h, the solution was filtered while warm and the filter cake was washed with warm EtOH (3 mL) to give (Z)-4-(7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)pyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile (76 mg, 80%) as a bright yellow solid. LCMS (ES): >90% pure, m/z 401 [M+1]+.

Aufarbeitung

  1. filtrationthe solution was filtered
  2. temperaturewhile warm
  3. washthe filter cake was washed with warm EtOH (3 mL)

Quellen und Nachweise

ORD-Eintrag
ord-06a7043127834a9984063e11cba05fc6
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575177B2

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