Water → HCID 53497453, Verbindung

HRID 1852975

Reaktionsgleichung

Reaktionsgleichung von HRID 1852975
[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[N:12]=[C:11]([C:13]3[CH:14]=[N:15][NH:16][CH:17]=3)[N:10]3[CH:18]=[CH:19][N:20]=[C:9]3[CH:8]=2)[CH:4]=[N:3]1.[CH2:21]1[CH2:31][CH2:30][N:29]2[C:24](=NCCC2)[CH2:23][CH2:22]1.C1(C=CC#N)CC1.O>CN(C=O)C>[CH:21]1([CH:22]([N:15]2[CH:14]=[C:13]([C:11]3[N:10]4[CH:18]=[CH:19][N:20]=[C:9]4[CH:8]=[C:7]([C:5]4[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=4)[N:12]=3)[CH:17]=[N:16]2)[CH2:23][C:24]#[N:29])[CH2:31][CH2:30]1

Komponenten

6

Edukt 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 670567823-Cyclopropylacrylonitrile2×HCID 67452537HCID 67452537, Verbindung

Produkt 1

HCID 53497453HCID 53497453, VerbindungAusbeute 23 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 7-(1-methyl-1H-pyrazol-4-yl)-5-(1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidine (Preparation; K-1; 0.130 g, 0.490 mmol) in dry DMF (2 mL) was added DBU (89.5 mg, 0.588 mmol) and 3-cyclopropylacrylonitrile (Preparation B; 0.183 g, 1.96 mmol). The reaction mixture was stirred at ambient temperature for 24 hours. Additional 3-cyclopropylacrylonitrile (0.046 g, 0.49 mmol) was added and the reaction mixture was stirred at ambient temperature for 72 hours. The reaction mixture was added to H2O (8 mL), mixed and extracted with EtOAc. The combined EtOAc extracts were washed with saturated NaCl and dried over MgSO4/activated carbon. The solution was eluted through a short SiO2 column (15 mL course frit funnel, ½ full of SiO2) eluting first with EtOAc, then with 10% MeOH/EtOAc. The 10% MeOH/EtOAc fraction was concentrated and the resulting residue treated with Et2O and sonicated to give a granular suspension. The precipitate was allowed to settle, Et2O decanted off, solid washed with Et2O and then dried under vacuum to provide a 3-cyclopropyl-3-(4-(7-(1-methyl-1H-pyrazol-4-yl)imidazo[1,2-c]pyrimidin-5-yl)-1H-pyrazol-1-yl)propanenitrile (40 mg, 23% yield) as a white powder. MS (apci) m/z=359.2 (M+H).

Aufarbeitung

  1. stirringthe reaction mixture was stirred at ambient temperature for 72 hours
  2. additionmixed
  3. extractionextracted with EtOAc
  4. washThe combined EtOAc extracts were washed with saturated NaCl
  5. dry with materialdried over MgSO4/activated carbon
  6. washThe solution was eluted through a short SiO2 column (15 mL course frit funnel, ½ full of SiO2)
  7. washeluting first with EtOAc
  8. concentrationThe 10% MeOH/EtOAc fraction was concentrated
  9. additionthe resulting residue treated with Et2O
  10. customsonicated
  11. customto give a granular suspension
  12. customEt2O decanted off
  13. washsolid washed with Et2O
  14. customdried under vacuum

Quellen und Nachweise

ORD-Eintrag
ord-f910b99949f64851adac2df01932446f
Quelldatensatz
uspto-grants-2015_02
Patentnummer
US08962596B2

Verknüpfte Notizen

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