Ethanol → tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(8-((R)-1-methoxypropan-2-yloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

HRID 338957Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338957
[F:1][C:2]([F:26])([F:25])[C@H:3]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13]1)[C:4]1[CH:5]=[N:6][C:7]([NH:10][NH2:11])=[CH:8][CH:9]=1.[CH3:27][O:28][CH2:29][C@H:30]([O:32][C:33]1[CH:34]=[CH:35][CH:36]=[C:37]2[C:42]=1[N:41]=[C:40]([CH:43]=O)[CH:39]=[CH:38]2)[CH3:31].C(O)C.C(O)(=O)C.C(O)(=O)C.I(C1C=CC=CC=1)=O.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[F:26][C:2]([F:25])([F:1])[C@H:3]([N:12]1[CH2:16][CH2:15][C@H:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:23])[CH3:21])[CH2:13]1)[C:4]1[CH:9]=[CH:8][C:7]2[N:6]([C:43]([C:40]3[CH:39]=[CH:38][C:37]4[C:42](=[C:33]([O:32][C@H:30]([CH3:31])[CH2:29][O:28][CH3:27])[CH:34]=[CH:35][CH:36]=4)[N:41]=3)=[N:11][N:10]=2)[CH:5]=1

Komponenten

7

Edukt 5

HCID 702EthanolHCID 516892Sodium BicarbonateHCID 73357407Acetic acid;iodosylbenzeneHCID 86707414tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamateHCID 86707475(R)-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde

Produkt 1

HCID 86707476tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(8-((R)-1-methoxypropan-2-yloxy)quinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamateAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(6-hydrazinylpyridin-3-yl)ethyl)pyrrolidin-3-ylcarbamate (0.33 g, 0.87 mmol) and (R)-8-(1-methoxypropan-2-yloxy)quinoline-2-carbaldehyde (0.21 g, 0.87 mmol) in ethanol (4.3 mL, 0.87 mmol) was allowed to stir at ambient temperature for 12 hours. The solvent was removed under reduced pressure. The residue was dissolved in dichloromethane (4.3 mL) and iodosobenzene diacetate (0.31 g, 0.95 mmol) was added. The reaction mixture was stirred at ambient temperature for 1 hour. Ethyl acetate (20 mL) and saturated sodium bicarbonate (10 mL) were added. The organic layer was separated, washed with brine, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by reverse phase chromatography on C18 (25-100% acetonitrile/water) to give the title compound (0.38 g, 73%).

Aufarbeitung

  1. customThe solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in dichloromethane (4.3 mL)
  3. stirringThe reaction mixture was stirred at ambient temperature for 1 hour
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by reverse phase chromatography on C18 (25-100% acetonitrile/water)

Quellen und Nachweise

ORD-Eintrag
ord-661e2350a71e41d3873925c15a000256
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

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