Acetic Acid → 3-Chloro-6-(4-cyclopropylpiperazin-1-yl)pyridazine

HRID 389043Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 389043
[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)=[CH:6][CH:7]=1.C(O[C:17]1(O[Si](C)(C)C)[CH2:19][CH2:18]1)C.C(O)(=O)C.C([BH3-])#N.[Na+]>C1COCC1.O>[Cl:1][C:2]1[N:3]=[N:4][C:5]([N:8]2[CH2:9][CH2:10][N:11]([CH:17]3[CH2:19][CH2:18]3)[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Komponenten

7

Edukt 4

HCID 176Acetic AcidHCID 2734686(1-Ethoxycyclopropoxy)trimethylsilaneHCID 5003444Sodium cyanoborohydrideHCID 52949263-chloro-6-(piperazin-1-yl)pyridazine

Produkt 1

HCID 614441503-Chloro-6-(4-cyclopropylpiperazin-1-yl)pyridazine

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
62 °C

Versuchsvorschrift

3-Chloro-6-piperazin-1-ylpyridazine (9.93 g, 50 mmol) was suspended in THF (80 mL), and water (18.9 mL), [(1-ethoxycyclopropyl)oxy]trimethylsilan (17.423 g, 100 mmol), acetic acid (8.5 mL, 150 mmol) and sodium cyanoborohydride (4.08 g, 65 mmol) were added. The mixture was heated at 62° C. for 16 h, solvents removed in vacuo and the remainder stirred with DCM (100 mL) and water (75 mL). The pH was adjusted to 10, the organic phase was separated, washed with water and dried over magnesium sulphate. Evaporation in vacuo yielded 3-chloro-6-(4-cyclopropylpiperazin-1-yl)pyridazine as a solid which was recrystallized from acetonitrile to yield the product, 8.18 g, 69%.

Aufarbeitung

  1. customsolvents removed in vacuo
  2. customthe organic phase was separated
  3. washwashed with water
  4. dry with materialdried over magnesium sulphate
  5. customEvaporation in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8072da4933424fddb9e03a81700415a0
Quelldatensatz
uspto-grants-2013_02
Patentnummer
US08378097B2

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