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Hydrochloric Acid → (6S)-3-(1,1-Difluoro-2-(((3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl)amino)ethyl)-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

HRID 588741
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 588741
Cl.[F:2][C:3]([C:26]1[CH:27]=[C:28]2[CH2:51][C@@:33]3([C:41]4[C:36](=[N:37][CH:38]=[CH:39][CH:40]=4)[N:35](COCC[Si](C)(C)C)[C:34]3=[O:50])[CH2:32][C:29]2=[N:30][CH:31]=1)([F:25])[CH2:4][NH:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C@@H:9]([CH3:18])[N:8]([CH2:19][C:20]([F:23])([F:22])[F:21])[C:7]1=[O:24].[OH-].[NH4+]>CO>[F:2][C:3]([C:26]1[CH:27]=[C:28]2[CH2:51][C@@:33]3([C:41]4[C:36](=[N:37][CH:38]=[CH:39][CH:40]=4)[NH:35][C:34]3=[O:50])[CH2:32][C:29]2=[N:30][CH:31]=1)([F:25])[CH2:4][NH:5][C@H:6]1[CH2:11][C@@H:10]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C@@H:9]([CH3:18])[N:8]([CH2:19][C:20]([F:23])([F:21])[F:22])[C:7]1=[O:24]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 14923Ammonium HydroxideHCID 131734441(6S)-3-(1,1-Difluoro-2-(((3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl)amino)ethyl)-1'((2-(trimethylsilyl)ethoxy)methyl)-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Produkt 1

HCID 72199094
(6S)-3-(1,1-Difluoro-2-(((3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl)amino)ethyl)-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3'-pyrrolo[2,3-b]pyridin]-2'(1'H)-one

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel2×

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

HCl gas was bubbled into a solution of (6S)-3-(1,1-difluoro-2-(((3S,5S,6R)-6-methyl-2-oxo-5-phenyl-1-(2,2,2-trifluoroethyl)piperidin-3-yl)amino)ethyl)-1′-((2-(trimethylsilyl)ethoxy)methyl)-5,7-dihydrospiro[cyclopenta[b]pyridine-6,3′-pyrrolo[2,3-b]pyridin]-2′(1′H)-one (0.012 g, 0.017 mmol) in MeOH (3 mL) cooled to 0° C. until saturated. The resulting mixture was stirred at 0° C. for 1 h and then concentrated to dryness in vacuo. To a solution of this crude mixture in MeOH (5 mL) was added ammonium hydroxide (0.047 mL, 0.335 mmol), and the reaction was stirred at ambient temperature for 30 min. The reaction was concentrated to dryness in vacuo. The crude product was purified by reverse-phase HPLC, eluting with 10% acetonitrile in water (0.1% TFA used as a modifier) initially, grading to 80% acetonitrile in water, to give the title compound. MS: m/z=586.2 (M+1). 1H NMR (500 MHz, CDCl3) δ 8.77 (s, 1H), 8.04 (d, 1H, J=7.0 Hz), 8.00 (s, 1H), 7.90 (bs, 1H), 7.61 (d, 1H, J=7.0 Hz), 7.40-7.29 (m, 3H), 7.26-7.10 (m, 3H), 4.87-4.81 (m, 1H), 4.07 (dd, 1H, J=11.4, 6.8 Hz), 3.98 (s, 2H), 3.90-3.75 (m, 3H), 3.73 (d, 1H, J=17.6 Hz), 3.57-3.48 (m, 2H), 3.38 (d, 1H, J=17.1 Hz), 3.35-3.27 (m, 1H), 2.63 (dt, 1H, J=12.5 Hz), 2.49-2.47 (m, 1H), 0.98 (d, 3H, J=6.5 Hz).

Aufarbeitung

  1. concentrationconcentrated to dryness in vacuo
  2. stirringthe reaction was stirred at ambient temperature for 30 min
  3. concentrationThe reaction was concentrated to dryness in vacuo
  4. customThe crude product was purified by reverse-phase HPLC
  5. washeluting with 10% acetonitrile in water (0.1% TFA

Quellen und Nachweise

ORD-Eintrag
ord-5cf315517cc34388a17812c67283c646
Quelldatensatz
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09227972B2

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