Hydrochloric Acid → N-[4-[(3S,5R)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(oxan-3-yloxy)phenyl]-5-fluoropyridine-2-carboxamide

HRID 1499618Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1499618
[F:1][C:2]1[CH:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][O:11][CH2:10]2)[CH:5]=[C:4]([F:15])[C:3]=1[C:16]1[N:21]=[C:20]([C:22]([NH:24][C:25]2[C:26]([N:35]3[CH2:40][C@H:39]([CH3:41])[CH2:38][C@H:37]([NH:42]C(=O)OC(C)(C)C)[CH2:36]3)=[C:27]3[CH2:33][CH2:32][CH:31]([OH:34])[C:28]3=[N:29][CH:30]=2)=[O:23])[CH:19]=[CH:18][C:17]=1[F:50].Cl.O1CCOCC1>>[NH2:42][C@H:37]1[CH2:38][C@@H:39]([CH3:41])[CH2:40][N:35]([C:26]2[C:25]([NH:24][C:22]([C:20]3[CH:19]=[CH:18][C:17]([F:50])=[C:16]([C:3]4[C:2]([F:1])=[CH:7][C:6]([O:8][CH:9]5[CH2:14][CH2:13][CH2:12][O:11][CH2:10]5)=[CH:5][C:4]=4[F:15])[N:21]=3)=[O:23])=[CH:30][N:29]=[C:28]3[CH:31]([OH:34])[CH2:32][CH2:33][C:27]=23)[CH2:36]1

Komponenten

4

Edukt 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 86726835tert-butyl ((3S,5R)-1-{3-[({6-[2,6-difluoro-4-(tetrahydro-2H-pyran-3-yloxy)phenyl]-5-fluoropyridin-2-yl}carbonyl)amino]-7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-4-yl}-5-methylpiperidin-3-yl)carbamate

Produkt 1

HCID 86726836N-[4-[(3S,5R)-3-amino-5-methylpiperidin-1-yl]-7-hydroxy-6,7-dihydro-5H-cyclopenta[b]pyridin-3-yl]-6-[2,6-difluoro-4-(oxan-3-yloxy)phenyl]-5-fluoropyridine-2-carboxamide

Versuchsvorschrift

The alcohol intermediate made above was treated with 4.0 M HCl in dioxane (1 mL, 5 mmol) at room temperature overnight. The solution was concentrated under reduced pressure and the resulting residue was purified by preparative LCMS (Waters SunFire™ C18 column, 19 mm×100 mm, 5 μm particle size, eluting with a gradient of MeCN/water containing 0.1% NH4OH, at flow rate of 30 mL/min.) to give two separated diastereoisomers of the title compound as white powders.

Aufarbeitung

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe resulting residue was purified by preparative LCMS (Waters SunFire™ C18 column, 19 mm×100 mm, 5 μm particle size
  3. washeluting with a gradient of MeCN/water containing 0.1% NH4OH, at flow rate of 30 mL/min.)

Quellen und Nachweise

ORD-Eintrag
ord-ff5feaa540ba402b96d56f400f66a9b6
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09200004B2

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