Phosphorus oxychloride → 4-Chloro-1-[2-(4-methylpiperazin-1-yl)ethyl]-5-phenyl-3-pyrrolidin-1-yl-pyrazolo[3,4-c]pyridazine

HRID 588582Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 588582
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][N:10]2[C:14]3[N:15]=[N:16][C:17]([C:20]4[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:18](O)[C:13]=3[C:12]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)=[N:11]2)[CH2:4][CH2:3]1.O=P(Cl)(Cl)[Cl:33]>C(Cl)Cl>[Cl:33][C:18]1[C:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)=[N:16][N:15]=[C:14]2[N:10]([CH2:9][CH2:8][N:5]3[CH2:4][CH2:3][N:2]([CH3:1])[CH2:7][CH2:6]3)[N:11]=[C:12]([N:26]3[CH2:30][CH2:29][CH2:28][CH2:27]3)[C:13]=12

Komponenten

4

Edukt 2

HCID 24813Phosphorus oxychlorideHCID 178480892HCID 178480892, Verbindung

Produkt 1

HCID 867172834-Chloro-1-[2-(4-methylpiperazin-1-yl)ethyl]-5-phenyl-3-pyrrolidin-1-yl-pyrazolo[3,4-c]pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

A suspension of 1-[2-(4-methylpiperazin-1-yl)ethyl]-5-phenyl-3-pyrrolidin-1-yl-pyrazolo[3,4-c]pyridazin-4-ol (90 mg) in POCl3 (6 mL) and CH2Cl2 (3 mL) was heated to 60° C. for 2.5 h. The mixture was concentrated in vacuo and the residue was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution. The layers were separated and the aqueous was extracted with CH2Cl2, the combined organics were dried (MgSO4), filtered and concentrated in vacuo. The residue was purified by preparative HPLC to provide Compound Iz (12 mg).

Aufarbeitung

  1. concentrationThe mixture was concentrated in vacuo
  2. customthe residue was partitioned between CH2Cl2 and sat. aq. NaHCO3 solution
  3. customThe layers were separated
  4. extractionthe aqueous was extracted with CH2Cl2
  5. dry with materialthe combined organics were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by preparative HPLC
  9. customto provide Compound Iz (12 mg)

Quellen und Nachweise

ORD-Eintrag
ord-97be80fc7468443ea8873da1bb30e91d
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09227976B2

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