Tetrahydrofuran → Benzyl [2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(1-hydroxy-1-methylethyl)quinolin-3-yl]carbamate

HRID 924392Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 924392
[C:1]([C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH:37][C:38]([O:40][CH2:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[O:39])[C:10]([C:14]([NH:16][C:17]3[CH:18]=[N:19][CH:20]=[CH:21][C:22]=3[N:23]3[CH2:28][CH2:27][CH2:26][C@H:25]([NH:29][C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33])[CH2:24]3)=[O:15])=[N:11]2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[CH2:48]1COCC1>C[Mg]Br.CCOC(C)=O.Cl>[C:32]([O:31][C:30]([NH:29][C@H:25]1[CH2:26][CH2:27][CH2:28][N:23]([C:22]2[CH:21]=[CH:20][N:19]=[CH:18][C:17]=2[NH:16][C:14]([C:10]2[C:9]([NH:37][C:38](=[O:39])[O:40][CH2:41][C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=3)=[CH:8][C:7]3[C:12](=[CH:13][C:4]([C:1]([OH:3])([CH3:48])[CH3:2])=[CH:5][CH:6]=3)[N:11]=2)=[O:15])[CH2:24]1)=[O:36])([CH3:35])([CH3:34])[CH3:33]

Komponenten

6

Edukt 2

HCID 8028Tetrahydrofuran2×HCID 86726872tert-Butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate

Produkt 1

HCID 90287190Benzyl [2-{[(4-{(3S)-3-[(tert-butoxycarbonyl)amino]piperidin-1-yl}pyridin-3-yl)amino]carbonyl}-7-(1-hydroxy-1-methylethyl)quinolin-3-yl]carbamateAusbeute 92 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 313Hydrochloric AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 178418573HCID 178418573, VerbindungLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a mixture of tert-butyl [(3S)-1-(3-{[(7-acetyl-3-{[(benzyloxy)carbonyl]amino}quinolin-2-yl)carbonyl]amino}pyridin-4-yl)piperidin-3-yl]carbamate (0.100 g, 0.156 mmol) in THF (4.0 mL), methylmagnesium bromide in THF (3.0 M, 0.43 mL, 1.3 mmol) was added slowly at 0° C. under nitrogen. The reaction mixture was stirred at 0° C. for 1 h and was then allowed to warm to room temperature. The reaction mixture was diluted with EtOAc (10 mL), and 1 M HCl was slowly added to adjust the pH to 7. The aqueous layer was extracted twice with EtOAc. The organic extracts were combined, dried over Na2SO4, filtered and concentrated under reduced pressure to give the sub-title compound (94 mg, 92%). LCMS calc. for C36H43N6O6 (M+H)+: m/z=655.2. Found: 655.1.

Aufarbeitung

  1. additionwas added slowly at 0° C. under nitrogen
  2. temperatureto warm to room temperature
  3. additionwas slowly added
  4. extractionThe aqueous layer was extracted twice with EtOAc
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-10920f94531d42d695822b70e8391cc9
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09278950B2

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