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Ammonium Chloride → HCID 86682466, Verbindung

HRID 715891
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 715891
[F:1][C:2]1([F:47])[CH2:7][CH2:6][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:20])([CH3:19])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([CH:33]=O)=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[CH:35]([F:46])[C:36]2[CH:41]=[CH:40][C:39]([C:42]([F:45])([F:44])[F:43])=[CH:38][CH:37]=2)[CH2:4][CH2:3]1.[CH3:48][NH2:49].CO.[BH4-].[Na+].[Cl-].[NH4+].C(=O)([O-])O.[Na+]>O1CCCC1.CO>[F:1][C:2]1([F:47])[CH2:3][CH2:4][CH:5]([C:8]2[C:17]3[CH:16]([OH:18])[CH2:15][C:14]([CH3:19])([CH3:20])[CH2:13][C:12]=3[N:11]=[C:10]([CH:21]3[CH2:26][CH2:25][N:24]([C:27]4[N:32]=[CH:31][C:30]([CH2:33][NH:49][CH3:48])=[CH:29][N:28]=4)[CH2:23][CH2:22]3)[C:9]=2[CH:35]([F:46])[C:36]2[CH:37]=[CH:38][C:39]([C:42]([F:45])([F:43])[F:44])=[CH:40][CH:41]=2)[CH2:6][CH2:7]1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 25517Ammonium ChlorideHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 57454252Monomethylamine methanolHCID 86682450HCID 86682450, Verbindung

Produkt 1

HCID 86682466HCID 86682466, Verbindung
Ausbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

To 165 mg (0.250 mmol) of 4-(4,4-Difluorocyclohexyl)-3-{fluoro[4-(trifluoromethyl)phenyl]methyl}-2-[1-(5-formyl pyrimidin-2-yl)piperidin-4-yl]-7,7-dimethyl-5,6,7,8-tetrahydroquinolin-5-ol, which was prepared by a method similar to that of Example (36-1), 1.0 ml of methanol, 0.1 ml of tetrahydrofuran and 0.20 ml (about 2.5 mmol) of about 40% methylamine-methanol solution were added, and the reaction solution was stirred at room temperature for 12 hours. Then, 95 mg (2.5 mmol) of sodium borohydride was added thereto and the reaction solution was stirred at room temperature for 1 hour. After completion of the reaction, saturated ammonium chloride aqueous solution was poured into the reaction solution until the bubbling disappeared. Saturated sodium hydrogencarbonate aqueous solution was poured into the reaction solution to make the reaction solution basic and the reaction solution was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride aqueous solution and dried with anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The obtained residue was subjected to silica gel column chromatography [dichloromethane/methanol/28% ammonia water=100/0/0-90/9.5/0.5 (V/V/V)] and the fraction including the desired compound was concentrated under reduced pressure to provide 128 mg of the title compound as a colorless oil (yield: 76%).

Aufarbeitung

  1. additionwere added
  2. stirringthe reaction solution was stirred at room temperature for 1 hour
  3. additionwas poured into the reaction solution until the bubbling
  4. extractionthe reaction solution was extracted with ethyl acetate
  5. washThe organic layer was washed with saturated sodium chloride aqueous solution
  6. dry with materialdried with anhydrous magnesium sulfate
  7. distillationthe solvent was distilled off under reduced pressure
  8. concentrationwas concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-ea5fba7579c14e4a9323503a7e1cc190
Quelldatensatz
uspto-grants-2015_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US09187450B2

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