Hydrochloric Acid → N-(1-Benzyl-4,4-diethoxy-piperidin-3-yl)-6-(2-ethyl-5-fluoro-4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboxamidine

HRID 2038713Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2038713
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])[CH:10]([NH:20][C:21]([C:23]2[C:31]3[C:26](=[CH:27][C:28]([C:32]4[CH:37]=[C:36]([F:38])[C:35]([O:39]COCC[Si](C)(C)C)=[CH:34][C:33]=4[CH2:48][CH3:49])=[CH:29][CH:30]=3)[N:25]([CH:50]3[CH2:55][CH2:54][CH2:53][CH2:52][O:51]3)[N:24]=2)=[NH:22])[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.C(=O)([O-])O.[Na+]>C(O)C>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([O:17][CH2:18][CH3:19])([O:14][CH2:15][CH3:16])[CH:10]([NH:20][C:21]([C:23]2[C:31]3[C:26](=[CH:27][C:28]([C:32]4[CH:37]=[C:36]([F:38])[C:35]([OH:39])=[CH:34][C:33]=4[CH2:48][CH3:49])=[CH:29][CH:30]=3)[N:25]([CH:50]3[CH2:55][CH2:54][CH2:53][CH2:52][O:51]3)[N:24]=2)=[NH:22])[CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 178467533N-(1-Benzyl-4,4-diethoxy-piperidin-3-yl)-6-[2-ethyl-5-fluoro-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboxamidine

Produkt 1

HCID 178467532N-(1-Benzyl-4,4-diethoxy-piperidin-3-yl)-6-(2-ethyl-5-fluoro-4-hydroxy-phenyl)-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboxamidineAusbeute 100,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

To a solution of N-(1-benzyl-4,4-diethoxy-piperidin-3-yl)-6-[2-ethyl-5-fluoro-4-(2-trimethylsilanyl-ethoxymethoxy)-phenyl]-1-(tetrahydro-pyran-2-yl)-1H-indazole-3-carboxamidine (Preparation 8, 7.28 g, 9.4 mmol) in ethanol (32 mL) was added concentrated hydrochloric acid (12M, 3.92 mL, 47 mmol) and the resulting solution was allowed to stir at room temperature for 18 hours. The reaction mixture was cooled to 0° C. and neutralised by dropwise addition of a saturated aqueous solution of sodium hydrogen carbonate (150 mL). The mixture was extracted with EtOAc (2×200 mL). The combined organic layers were washed with further saturated aqueous sodium hydrogen carbonate solution (100 mL), dried over MgSO4 and concentrated in vacuo to give the title compound as a foam (6.06 g).

Aufarbeitung

  1. extractionThe mixture was extracted with EtOAc (2×200 mL)
  2. washThe combined organic layers were washed with further saturated aqueous sodium hydrogen carbonate solution (100 mL)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-982dbeea36ed4d5eab9fffde18943d6d
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08575336B2

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