Ethyl Acetate → N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxyazetidin-1-yl)-5-iodonicotinamide

HRID 525766Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 525766
[OH:1][CH:2]1[CH2:5][NH:4][CH2:3]1.CCN(C(C)C)C(C)C.Cl[C:16]1[C:35]([I:36])=[CH:34][C:19]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]([Cl:33])([F:32])[F:31])=[CH:25][CH:24]=2)=[O:21])=[CH:18][N:17]=1.CCOC(C)=O>CC(O)C>[Cl:33][C:30]([F:31])([F:32])[O:29][C:26]1[CH:27]=[CH:28][C:23]([NH:22][C:20](=[O:21])[C:19]2[CH:34]=[C:35]([I:36])[C:16]([N:4]3[CH2:5][CH:2]([OH:1])[CH2:3]3)=[N:17][CH:18]=2)=[CH:24][CH:25]=1

Komponenten

6

Edukt 4

HCID 8857Ethyl AcetateHCID 81531DiisopropylethylamineHCID 15142903-HydroxyazetidineHCID 867026266-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide

Produkt 1

HCID 89906873N-(4-(chlorodifluoromethoxy)phenyl)-6-(3-hydroxyazetidin-1-yl)-5-iodonicotinamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 3776IsopropanolLösungsmittel

Reaktionsbedingungen

Temperatur
140 °C

Versuchsvorschrift

3-Hydroxyazetidine (164 mg, 2.18 mmol) and DIPEA (0.419 mL, 2.396 mmol) were added to a suspension of 6-chloro-N-(4-(chlorodifluoromethoxy)phenyl)-5-iodonicotinamide (Stage 48.3, 500 mg, 1.089 mmol) in iPrOH (2 mL). and stirred at 140° C. for 16 h. EtOAc (80 mL) was added and the solution was washed with 1 M HCl (30 mL), aq. sat. NaHCO3 solution (30 mL) and water (30 mL), dried over Na2SO4 and the solvent was evaporated off under reduced pressure to give the title product as yellow foam. HPLC (Condition 7) tR=6.64 min, UPLC-MS (Condition 3) tR=1.08 min, m/z=496.0/498.0 [M+H]+.

Aufarbeitung

  1. washthe solution was washed with 1 M HCl (30 mL), aq. sat. NaHCO3 solution (30 mL) and water (30 mL)
  2. dry with materialdried over Na2SO4
  3. customthe solvent was evaporated off under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-569f44f37d154022924c3a51556c3a5c
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340537B2

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