Piperidine → HCID 178429911, Verbindung

HRID 2037030

Reaktionsgleichung

Reaktionsgleichung von HRID 2037030
[NH:1]1[CH2:7][C:5](=[O:6])[NH:4][C:2]1=[O:3].[Cl:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[NH:17][C:18]1[C:23]([CH3:24])=[C:22]([NH:25][CH:26]2[CH2:28][CH2:27]2)[N:21]2[N:29]=[CH:30][C:31]([CH:32]=O)=[C:20]2[N:19]=1)[C:12]#[N:13].N1CCCCC1>C(O)C.O>[Cl:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[NH:17][C:18]1[C:23]([CH3:24])=[C:22]([NH:25][CH:26]2[CH2:27][CH2:28]2)[N:21]2[N:29]=[CH:30][C:31]([CH:32]=[C:7]3[C:5](=[O:6])[NH:4][C:2](=[O:3])[NH:1]3)=[C:20]2[N:19]=1)[C:12]#[N:13]

Komponenten

6

Edukt 3

HCID 8082PiperidineHCID 10006HydantoinHCID 583137103-Chloro-4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile

Produkt 1

HCID 178429911HCID 178429911, VerbindungAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

Hydantoin (2.7 mg, 0.027 mmol) and 3-chloro-4-(7-(cyclopropylamino)-3-formyl-6-methylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile (10 mg, 0.027 mmol) were dissolved in ethanol (0.4 mL) along with piperidine (3 uL, 0.03 mmol). The reaction was heated at 80° C. After 10 hours, the reaction was cooled to r.t., diluted with water, and the precipitate was collected and washed with water, 1:1 ethanol:water, then ethanol. The bright yellow solid was dried in vacuo to give 3-chloro-4-(7-(cyclopropylamino)-3-((2,5-dioxoimidazolidin-4-ylidene)methyl)-6-methylpyrazolo[1,5-a]pyrimidin-5-ylamino)benzonitrile (7 mg, 58% yield). LCMS (M+1=449)

Aufarbeitung

  1. temperaturethe reaction was cooled to r.t.
  2. customthe precipitate was collected
  3. washwashed with water, 1:1 ethanol
  4. customThe bright yellow solid was dried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-36734d2ab37a4067bcbe26efe2e81833
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575177B2

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