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Triethylamine → N-((1R,3S)-3-Isopropyl-3-{[5-(trifluoromethyl)-3',6'-dihydro-3,4'-bipyridin-1'(2'H)-yl]carbonyl}cyclopentyl)-3-methoxytetrahydro-2H-pyran-4-amine

HRID 1044596
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1044596
[CH:1]([C@:4]1([C:10]([N:12]2[CH2:17][CH:16]=[C:15]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=3)[CH2:14][CH2:13]2)=[O:11])[CH2:8][CH2:7][C@@H:6]([NH2:9])[CH2:5]1)([CH3:3])[CH3:2].[CH3:28][O:29][CH:30]1[C:35](=O)[CH2:34][CH2:33][O:32][CH2:31]1.C(N(CC)CC)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C(Cl)Cl>[CH:1]([C@:4]1([C:10]([N:12]2[CH2:13][CH:14]=[C:15]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([C:24]([F:27])([F:26])[F:25])[CH:23]=3)[CH2:16][CH2:17]2)=[O:11])[CH2:8][CH2:7][C@@H:6]([NH:9][CH:35]2[CH2:34][CH2:33][O:32][CH2:31][CH:30]2[O:29][CH3:28])[CH2:5]1)([CH3:3])[CH3:2]
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Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 235336103-Methoxyoxan-4-oneHCID 57938709HCID 57938709, Verbindung

Produkt 1

HCID 57938717N-((1R,3S)-3-Isopropyl-3-{[5-(trifluoromethyl)-3',6'-dihydro-3,4'-bipyridin-1'(2'H)-yl]carbonyl}cyclopentyl)-3-methoxytetrahydro-2H-pyran-4-amineAusbeute 14 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a solution of (1R,3S)-3-isopropyl-3-{[5-(trifluoromethyl)-3′,6′-dihydro-3,4′-bipyridin-1′(2′H)-yl]carbonyl}cyclopentanamine (9.0 mg, 0.024 mmol), 3-methoxytetrahydro-4H-pyran-4-one (12.3 mg, 0.0709 mmol) and triethylamine (6.58 μL, 0.0472 mmol) in dry methylene chloride (2.0 mL) was added sodium triacetoxyborohydride (15.0 mg, 0.0708 mmol). After being stirred at room temperature overnight, the reaction was quenched with aqueous NaHCO3 and diluted with methylene chloride. The organic layer was separated and the aqueous layer was extracted with methylene chloride three times. The organic layers were combined, dried over MgSO4, filtered and evaporated under reduced pressure. The crude product (45 mg) was purified by silica gel column (30:70 MeOH/EtOAc) to provide 1.6 mg (14%) of pure product. LC-MS calculated for C26H36F3N3O3: (M+H) 496; found 496.1.

Aufarbeitung

  1. customthe reaction was quenched with aqueous NaHCO3
  2. additiondiluted with methylene chloride
  3. customThe organic layer was separated
  4. extractionthe aqueous layer was extracted with methylene chloride three times
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customevaporated under reduced pressure
  8. customThe crude product (45 mg) was purified by silica gel column (30:70 MeOH/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-de23712746a44be7aa36af5cd0a1d74d
Quelldatensatz
uspto-grants-2013_10
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08563582B2

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