Hydrochloric Acid → HCID 67373992, Verbindung

HRID 2168724Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2168724
[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 (1 H, s), 7.89 (1 H, s), 6.97 (2 H, s), 6.81 (1 H, s), 5.60 (1 H, bs), 4.37-4.43 (1 H, m), 3.10-3.45 (4 H, m), 2.90-2.95 (2 H, m), 2.81 (3 H, s), 2.35-2.61 (4 H, m), 2.23 (3 H, s), 1.25-1.87 (14 H, m), 0.83 (3 H, 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-969a85afc1874ceb81221afe41f7bd5f
Quelldatensatz
uspto-grants-2015_06
Patentnummer
US09045461B2

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