Diisopropylethylamine → (S)-1-(3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-3-amine

HRID 1483856Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1483856
Cl[C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[CH:9][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([Cl:17])[CH:12]=3)=[C:4]2[N:3]=1.[NH:18]1[CH2:23][CH2:22][CH2:21][C@H:20]([NH2:24])[CH2:19]1.CCN(C(C)C)C(C)C>CC(O)C.C([O-])(O)=O.[Na+]>[Cl:17][C:13]1[CH:12]=[C:11]([C:10]2[CH:9]=[N:8][N:5]3[CH:6]=[CH:7][C:2]([N:18]4[CH2:23][CH2:22][CH2:21][C@H:20]([NH2:24])[CH2:19]4)=[N:3][C:4]=23)[CH:16]=[CH:15][CH:14]=1

Komponenten

6

Edukt 3

HCID 81531DiisopropylethylamineHCID 855017(S)-piperidin-3-amineHCID 596622385-Chloro-3-(3-chloro-phenyl)-pyrazolo[1,5-a]pyrimidine

Produkt 1

HCID 71227735(S)-1-(3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-3-amineAusbeute 28,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776IsopropanolLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

A mixture of 5-chloro-3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidine (100 mg, 0.379 mmol), (S)-piperidin-3-amine (76 mg, 0.757 mmol), and DIEA (0.158 ml, 1.515 mmol) in 2-propanol (3 ml) was irradiated to 150° C. for 14 h in a Biotage microwave. After cooling, the mixture was diluted with saturated aqueous NaHCO3, and extracted three times with EtOAc. The combined extracts were washed with brine, dried over Na2SO4 and concentrated in vacuo. After absorbing on celite, the compound was purified by chromatography (12 g silica, 0-15% methanol/DCM) to give (S)-1-(3-(3-chlorophenyl)pyrazolo[1,5-a]pyrimidin-5-yl)piperidin-3-amine (35 mg, 28% yield) as a white solid.

Aufarbeitung

  1. customwas irradiated to 150° C. for 14 h in a Biotage microwave
  2. temperatureAfter cooling
  3. extractionextracted three times with EtOAc
  4. washThe combined extracts were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo
  7. customAfter absorbing on celite
  8. customthe compound was purified by chromatography (12 g silica, 0-15% methanol/DCM)

Quellen und Nachweise

ORD-Eintrag
ord-c089f007be924e35bc47003db6b89271
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09416132B2

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