Hydrochloric Acid → HCID 67373992, Verbindung

HRID 1972002Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1972002
[ClH:1].Cl.Cl.[CH2:4]([C:8]1[N:9]=[N:10][C:11]([O:28][CH:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[CH:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:18]([NH2:20])[CH:19]=1)[CH2:5][CH2:6][CH3:7].[C:36]([Cl:39])(=[O:38])[CH3:37].CCN(C(C)C)C(C)C.Cl>C(Cl)Cl.CN(C1C=CN=CC=1)C.CCOCC>[ClH:39].[ClH:1].[CH2:4]([C:8]1[N:9]=[N:10][C:11]([O:28][CH:29]2[CH2:34][CH2:33][N:32]([CH3:35])[CH2:31][CH2:30]2)=[CH:12][C:13]=1[C:14]1[CH:15]=[CH:16][C:17]([O:21][CH:22]2[CH2:27][CH2:26][CH2:25][CH2:24][CH2:23]2)=[C:18]([NH:20][C:36](=[O:38])[CH3:37])[CH:19]=1)[CH2:5][CH2:6][CH3:7]

Komponenten

8

Edukt 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 67374073HCID 67374073, Verbindung

Produkt 1

HCID 67373992HCID 67373992, VerbindungAusbeute 55,1 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 3283Diethyl EtherLösungsmittelHCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

To a solution of 5-[3-butyl-6-(1-methyl-piperidin-4-yloxy)-pyridazin-4-yl]-2-cyclohexyloxy-phenylamine trihydrochloride (0.2 mmol, 110 mg) in DCM (1.0 mL) at 0° C. was added acetyl chloride (0.4 mmol, 29 μL), DIEA (0.4 mmol, 70 μL) and DMAP (5 mg). And the mixture was stirred at room temperature for 1 hour. It was then condensed in vacuo and the residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH) to give a colorless sticky solid, which was dissolved in DCM (1.0 mL), 2N HCl in ether (1.0 mL) was added, kept at room temperature for 10 min, condensed, triturated with hexanes to provide the title compound (61 mg). LCMS: m/z 482 [M+1]. 1H NMR (400 MHz, CDCl3): δ 8.43 (1H, s), 7.89 (1H, s), 6.97 (2H, s), 6.81 (1H, s), 5.60 (1H, bs), 4.37-4.43 (1H, m), 3.10-3.45 (4H, m), 2.90-2.95 (2H, m), 2.81 (3H, s), 2.35-2.61 (4H, m), 2.23 (3H, s), 1.25-1.87 (14H, m), 0.83 (3H, t).

Aufarbeitung

  1. customcondensed in vacuo
  2. customthe residue was purified by silica gel chromatography (DCM to DCM+10% 2N NH3 in MeOH)
  3. customto give a colorless sticky solid, which
  4. waitkept at room temperature for 10 min
  5. customcondensed
  6. customtriturated with hexanes

Quellen und Nachweise

ORD-Eintrag
ord-e11fb8e592434f09912daaad192fd698
Quelldatensatz
uspto-grants-2013_04
Patentnummer
US08431575B2

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