Acetonitrile → 3-Cyclopropyl-3-(3-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile

HRID 1853058

Reaktionsgleichung

Reaktionsgleichung von HRID 1853058
Cl.[CH3:2][N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[C:12]([C:14]3[CH:18]=[CH:17][NH:16][N:15]=3)[N:11]3[CH:19]=[CH:20][N:21]=[C:10]3[CH:9]=2)[CH:5]=[N:4]1.[CH:22]1([CH:25]=[CH:26][C:27]#[N:28])[CH2:24][CH2:23]1.C(#N)C.C1CCN2C(=NCCC2)CC1>>[CH:22]1([CH:25]([N:16]2[CH:17]=[CH:18][C:14]([C:12]3[N:11]4[CH:19]=[CH:20][N:21]=[C:10]4[CH:9]=[C:8]([C:6]4[CH:5]=[N:4][N:3]([CH3:2])[CH:7]=4)[N:13]=3)=[N:15]2)[CH2:26][C:27]#[N:28])[CH2:24][CH2:23]1

Komponenten

5

Edukt 4

HCID 6342AcetonitrileHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 670567823-CyclopropylacrylonitrileHCID 178478909HCID 178478909, Verbindung

Produkt 1

HCID 682307973-Cyclopropyl-3-(3-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrileAusbeute 17,5 %

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

7-(1-Methyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-3-yl)imidazo[1,2-c]pyrimidine hydrochloride (Example 129, Step C, 50.2 mg, 0.148 mmol) and 3-cyclopropylacrylonitrile (Preparation B; 69.1 mg, 0.742 mmol) were suspended in acetonitrile (742 μL, 0.148 mmol). DBU (88.8 μL, 0.594 mmol) was added to the reaction mixture and heated at 45° C. for 15 hours. The reaction mixture was purified by reverse phase HPLC using a 0-100% acetonitrile/water gradient. The resultant solid was diluted in Et2O, sonicated, filtered and washed with Et2O to afford the title compound as a light yellow solid (9.3 mg, 17% yield). MS (apci) m/z=359.2 (M+H).

Aufarbeitung

  1. customThe reaction mixture was purified by reverse phase HPLC
  2. additionThe resultant solid was diluted in Et2O
  3. customsonicated
  4. filtrationfiltered
  5. washwashed with Et2O

Quellen und Nachweise

ORD-Eintrag
ord-b6d64f41f3874e56a935d3b0ff34dff9
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962596B2

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