Hydrochloric Acid → 4-Cyano-N-(1-(6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl)piperidin-4-yl)-N-methylbenzamide hydrochloride

HRID 1890773Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1890773
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([N:9]2[CH2:14][CH2:13][CH:12]([NH:15][CH3:16])[CH2:11][CH2:10]2)[N:5]=[N:4][C:3]=1[C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=1.C(N(CC)CC)C.[C:32]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([Cl:40])=[O:39])=[CH:36][CH:35]=1)#[N:33].Cl>C(Cl)Cl.CO>[ClH:40].[C:32]([C:34]1[CH:42]=[CH:41][C:37]([C:38]([N:15]([CH:12]2[CH2:13][CH2:14][N:9]([C:6]3[N:5]=[N:4][C:3]([C:17]4[CH:18]=[CH:19][C:20]([C:21]#[N:22])=[CH:23][CH:24]=4)=[C:2]([CH3:1])[C:7]=3[CH3:8])[CH2:10][CH2:11]2)[CH3:16])=[O:39])=[CH:36][CH:35]=1)#[N:33]

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 801724-Cyanobenzoyl chlorideHCID 67370777HCID 67370777, Verbindung

Produkt 1

HCID 462033944-Cyano-N-(1-(6-(4-cyanophenyl)-4,5-dimethylpyridazin-3-yl)piperidin-4-yl)-N-methylbenzamide hydrochlorideAusbeute 95,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Treat a solution of 4-(4,5-dimethyl-6-(4-(methylamino)piperidin-1-yl)pyridazin-3-yl)benzonitrile (90 mg, 0.28 mmol) and triethylamine (0.12 mL, 0.84 mmol) in CH2Cl2 (2.8 mL) with 4-cyanobenzoyl chloride (56 mg, 0.34 mmol). Stir the reaction at ambient temperature overnight. Wash with H2O and separate the layers. Directly purify the organic layer by flash silica gel chromatography (gradient of 0 to 2% 2 M NH3/MeOH in CH2Cl2). Concentrate to afford a white solid. Dissolve the material in MeOH and add 1.1 eq of methanolic HCl (preform by dripping acetyl chloride into MeOH). Concentrate the mixture under a stream of N2 gas and dry the residue in a vacuum oven at 45° C. to obtain the title compound as yellow solid (130 mg, 95%). ES/MS m/z 451.2 (M+1).

Aufarbeitung

  1. customthe reaction at ambient temperature overnight
  2. washWash with H2O
  3. customseparate the layers
  4. customDirectly purify the organic layer by flash silica gel chromatography (gradient of 0 to 2% 2 M NH3/MeOH in CH2Cl2)
  5. concentrationConcentrate
  6. customto afford a white solid
  7. concentrationConcentrate the mixture under a stream of N2 gas
  8. customdry the residue in a vacuum oven at 45° C.

Quellen und Nachweise

ORD-Eintrag
ord-11ae18646b0e4ecba4a41d04ad6a14b6
Quelldatensatz
uspto-grants-2013_08
Patentnummer
US08507490B2

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