Acetamide → HCID 59631275, compound

HRID 1431768Notes

Reaction equation

HRID 1431768 reaction equation
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

Participants

6

Reactant 3

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

Product 1

HCID 59631275HCID 59631275, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

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).

Workup

  1. customPrepared
  2. customPurification by reverse-phase HPLC

Sources & evidence

ORD record
ord-5478625ffa8c427db77b3ed1eb073a87
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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