Acetamide → HCID 59631275, Verbindung

HRID 1431768Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1431768
Cl[C:2]1[CH:3]=[C:4]([CH:14]([C:16]2[C:25]3[C:20](=[CH:21][C:22]([F:26])=[CH:23][CH:24]=3)[N:19]=[C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)[C:17]=2[CH3:33])[OH:15])[CH:5]=[C:6]([N:8]2[CH2:13][CH2:12][O:11][CH2:10][CH2:9]2)[CH:7]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].[C:42]([NH2:45])(=[O:44])[CH3:43]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)(C)C>[F:26][C:22]1[CH:21]=[C:20]2[C:25]([C:16]([CH:14]([OH:15])[C:4]3[CH:3]=[C:2]([NH:45][C:42](=[O:44])[CH3:43])[CH:7]=[C:6]([N:8]4[CH2:13][CH2:12][O:11][CH2:10][CH2:9]4)[CH:5]=3)=[C:17]([CH3:33])[C:18]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][N:28]=3)=[N:19]2)=[CH:24][CH:23]=1

Komponenten

6

Edukt 3

HCID 178AcetamideHCID 62657Potassium Phosphate, TribasicHCID 59631266HCID 59631266, Verbindung

Produkt 1

HCID 59631275HCID 59631275, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 6386tert-ButanolLösungsmittel

Versuchsvorschrift

Prepared according to Procedure W by stirring palladium (II) acetate (1.5 mg, 6.70 μmol), tetramethyl tert-butyl XPhos (9.7 mg, 0.020 mmol), (3-chloro-5-morpholinophenyl)(7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)methanol (0.031 g, 0.067 mmol), tripotassium phosphate (0.020 g, 0.094 mmol), acetamide (4.8 mg, 0.080 mmol), and tert-butanol (0.9 mL) at 110° C. for 1 hour. Purification by reverse-phase HPLC afforded N-(3-((7-fluoro-3-methyl-2-(pyridin-2-yl)quinolin-4-yl)(hydroxy)methyl)-5-morpholinophenyl)acetamide as a white amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.67 (1H, s), 8.70 (1H, d), 8.39 (1H, m), 8.02 (1H, t), 7.80 (1H, d), 7.70 (1H, d), 7.52 (1H, m), 7.39 (1H, t), 7.32 (1H, s), 6.87 (1H, s), 6.60 (1H, s), 6.52 (1H, d), 6.48 (1H, s), 3.72 (4H, t, J=4.7 Hz), 3.03 (4H, d, J=3.3 Hz), 2.47 (3H, s), 1.91 (3H, s). Mass Spectrum (ESI) m/e=467.2 (M+1).

Aufarbeitung

  1. customPrepared
  2. customPurification by reverse-phase HPLC

Quellen und Nachweise

ORD-Eintrag
ord-5478625ffa8c427db77b3ed1eb073a87
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940724B2

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