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Triethylamine → (3R,4R)-2-(3,4-Dihydroxypyrrolidin-1-yl)-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile

HRID 640727
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 640727
Cl[C:2]1[C:11]([C:12]#[N:13])=[C:10]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=2)[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:21][CH3:22])[CH:8]=2)[N:3]=1.[OH:23][C@H:24]1[C@H:28]([OH:29])[CH2:27][NH:26][CH2:25]1.C(N(CC)CC)C>CC(O)C.CCOC(C)=O>[OH:23][C@H:24]1[C@H:28]([OH:29])[CH2:27][N:26]([C:2]2[C:11]([C:12]#[N:13])=[C:10]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([F:20])[CH:15]=3)[C:9]3[C:4](=[CH:5][CH:6]=[C:7]([O:21][CH3:22])[CH:8]=3)[N:3]=2)[CH2:25]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 8471Triethylamine2×HCID 113703952-Chloro-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrileHCID 11499204(3R,4R)-pyrrolidine-3,4-diol2×

Produkt 1

HCID 11463095(3R,4R)-2-(3,4-Dihydroxypyrrolidin-1-yl)-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 3776
Isopropanol
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
150 °C

Versuchsvorschrift

A solution of 2-chloro-4-(3-fluorophenyl)-6-methoxyquinoline-3-carbonitrile (61.0 mg, 0.20 mmol), (3R,4R)-3,4-dihydroxypyrrolidine (43 mg, 0.42 mmol) and triethylamine (0.055 mL, 0.42 mmol) in 3 mL of 2-propanol was heated in a sealed tube at 120° C. for 3 days. The temperature was raised to 150° C. After 3 days, additional portions of (3R,4R)-3,4-dihydroxypyrrolidine (40 mg) and triethylamine (0.055 mL) were added. After a total of 11 days, the solution was cooled and diluted with EtOAc. The organic layer was washed with saturated NaHCO3 solution and brine, and dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by recrystallization from EtOAc/hexane (40 mg, 54%). Proton NMR for the product was consistent with the titled compound. HRMS (ES) exact mass calculated for C21H19FN3O3 (M+M+): 380.1405. Found 380.1401.

Aufarbeitung

  1. temperatureAfter a total of 11 days, the solution was cooled
  2. washThe organic layer was washed with saturated NaHCO3 solution and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified by recrystallization from EtOAc/hexane (40 mg, 54%)

Quellen und Nachweise

ORD-Eintrag
ord-f19199f70c354cd69467086bdc40cb5d
Quelldatensatz
uspto-grants-2010_04
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07692017B2

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