2-Methylpiperazine, (S)- → (S)-1-chloro-4-(3-methylpiperazin-1-yl)pyrido[3,4-d]pyridazine

HRID 1514365Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1514365
[Cl:1][C:2]1[N:7]=[N:6][C:5](Cl)=[C:4]2[CH:9]=[N:10][CH:11]=[CH:12][C:3]=12.[CH3:13][C@H:14]1[CH2:19][NH:18][CH2:17][CH2:16][NH:15]1>CN1C(=O)CCC1.O>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:18]2[CH2:17][CH2:16][NH:15][C@@H:14]([CH3:13])[CH2:19]2)=[C:4]2[CH:9]=[N:10][CH:11]=[CH:12][C:3]=12

Komponenten

5

Edukt 2

HCID 27342192-Methylpiperazine, (S)-HCID 122244971,4-Dichloropyrido[4,3-d]pyridazine

Produkt 1

HCID 57657608(S)-1-chloro-4-(3-methylpiperazin-1-yl)pyrido[3,4-d]pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 13387N-methyl-2-pyrrolidoneLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

To 1,4-dichloropyrido[3,4-d]pyridazine 3 (0.500 g, 2.50 mmol) in NMP (2.5 ml) was added (S)-2-methylpiperazine (0.300 g, 3.00 mmol). The reaction was stirred at 25° C. for 2 h. After one hour reaction contents were diluted with water (20×) and extracted with 10% MeOH in CH2Cl2 (3×25 mL). The combined organics were dried with Na2SO4 and concentrated in vacuo. Silica gel chromatography (gradient elution 0 to 5% MeOH in CH2Cl2) afforded (S)-1-chloro-4-(3-methylpiperazin-1-yl)pyrido[3,4-d]pyridazine 4 plus 10-15% substitution at the 4-position. 1H NMR (CDCl3) δ 9.48 (s, 1H), 9.03 (d, J=5.5 Hz, 1H), 7.94 (d, J=5.5 Hz, 1H) 3.96 (m, 2H), 3.11-3.88 (m, 5H), 2.93 (dd, J=12.8, 10.4, 1H). MS (calc'd) 263.1 (M+H, found) 264.1.

Aufarbeitung

  1. customAfter one hour reaction contents
  2. extractionextracted with 10% MeOH in CH2Cl2 (3×25 mL)
  3. dry with materialThe combined organics were dried with Na2SO4
  4. concentrationconcentrated in vacuo
  5. washSilica gel chromatography (gradient elution 0 to 5% MeOH in CH2Cl2)

Quellen und Nachweise

ORD-Eintrag
ord-70ef91fd17d3432da18b36d38e82a453
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222251B2

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