Hydrogen Bromide → 3-Amino-N-{4-[(3S,5R)-3-amino-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}-7-(4-methylpiperazin-1-yl)quinoline-2-carboxamide

HRID 924464Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924464
C(OC([NH:8][C@H:9]1[CH2:14][C@@H:13]([C:15]([F:18])([F:17])[F:16])[CH2:12][N:11]([C:19]2[CH:24]=[CH:23][N:22]=[CH:21][C:20]=2[NH:25][C:26]([C:28]2[C:37]([NH:38]C(=O)OCC3C=CC=CC=3)=[CH:36][C:35]3[C:30](=[CH:31][C:32]([N:49]4[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]4)=[CH:33][CH:34]=3)[N:29]=2)=[O:27])[CH2:10]1)=O)(C)(C)C.Br>CC(O)=O>[NH2:38][C:37]1[C:28]([C:26]([NH:25][C:20]2[CH:21]=[N:22][CH:23]=[CH:24][C:19]=2[N:11]2[CH2:12][C@H:13]([C:15]([F:17])([F:18])[F:16])[CH2:14][C@H:9]([NH2:8])[CH2:10]2)=[O:27])=[N:29][C:30]2[C:35]([CH:36]=1)=[CH:34][CH:33]=[C:32]([N:49]1[CH2:54][CH2:53][N:52]([CH3:55])[CH2:51][CH2:50]1)[CH:31]=2

Komponenten

4

Edukt 2

HCID 260Hydrogen BromideHCID 86726907Benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(4-methylpiperazin-1-yl)quinolin-3-yl]carbamate

Produkt 1

HCID 867269083-Amino-N-{4-[(3S,5R)-3-amino-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}-7-(4-methylpiperazin-1-yl)quinoline-2-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A mixture of benzyl [2-[({4-[(3S,5R)-3-[(tert-butoxycarbonyl)amino]-5-(trifluoromethyl)piperidin-1-yl]pyridin-3-yl}amino)carbonyl]-7-(4-methylpiperazin-1-yl)quinolin-3-yl]carbamate (0.006 g, 0.008 mmol) and 2 mL of 4.0 M HBr in AcOH was stirred at room temperature for 2 h. The mixture was concentrated under reduced pressure, and the residue was then treated with 4.5 mL of MeOH and 0.5 mL of NH4OH solution. The mixture was filtered and the filtrate was purified by preparative HPLC (XBridge™ C18 column, eluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 30 mL/min.) to afford the title compound. LCMS calc. for C26H32F3N8O [M+H]+: m/z=529.3. found: 529.3.

Aufarbeitung

  1. concentrationThe mixture was concentrated under reduced pressure
  2. additionthe residue was then treated with 4.5 mL of MeOH and 0.5 mL of NH4OH solution
  3. filtrationThe mixture was filtered
  4. customthe filtrate was purified by preparative HPLC (XBridge™ C18 column
  5. washeluting with a gradient of MeCN/water containing 0.1% NH4OH, at a flow rate of 30 mL/min.)

Quellen und Nachweise

ORD-Eintrag
ord-433119c22dac47329c3107980a1cb71e
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278950B2

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