Potassium Carbonate → N-(3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)phenyl)acetamide

HRID 1431756Notes

Reaction equation

HRID 1431756 reaction equation
CC(C1C=C(C(C)C)C(C2C=CC=CC=2P(C2CCCCC2)C2CCCCC2)=C(C(C)C)C=1)C.Cl[C:36]1[C:45]2[C:40](=[CH:41][C:42]([F:46])=[CH:43][CH:44]=2)[N:39]=[C:38]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=2)[C:37]=1[CH3:53].[NH2:54][C:55]1[CH:56]=[C:57]([NH:67][C:68](=[O:70])[CH3:69])[CH:58]=[C:59]([N:61]2[CH2:66][CH2:65][O:64][CH2:63][CH2:62]2)[CH:60]=1.C(=O)([O-])[O-].[K+].[K+]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C(O)(C)(C)C>[F:46][C:42]1[CH:41]=[C:40]2[C:45]([C:36]([NH:54][C:55]3[CH:56]=[C:57]([NH:67][C:68](=[O:70])[CH3:69])[CH:58]=[C:59]([N:61]4[CH2:66][CH2:65][O:64][CH2:63][CH2:62]4)[CH:60]=3)=[C:37]([CH3:53])[C:38]([C:47]3[CH:52]=[CH:51][CH:50]=[CH:49][N:48]=3)=[N:39]2)=[CH:44][CH:43]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 596310754-Chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinolineHCID 67507700N-(3-amino-5-morpholinophenyl)acetamide

Product 1

HCID 59631560N-(3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)phenyl)acetamide

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

Prepared according to Procedure X using palladium (II) acetate (2.1 mg, 9.17 μmol), XPhos (0.013 g, 0.028 mmol), 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.050 g, 0.183 mmol), N-(3-amino-5-morpholinophenyl)acetamide (0.043 g, 0.183 mmol), potassium carbonate (0.063 g, 0.458 mmol), and tert-butanol (0.5 mL). Purification by column chromatography (silica; 0-5% methanol in DCM) afforded N-(3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)phenyl)acetamide as a yellow amorphous solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 9.59 (1H, s), 8.68-8.71 (1H, m), 8.43 (1H, s), 8.08 (1H, dd, J=9.3, 6.2 Hz), 7.98 (1H, dd, J=7.7, 1.9 Hz), 7.83-7.87 (1H, m), 7.68-7.76 (1H, m), 7.44-7.51 (2H, m), 6.80-6.83 (1H, m), 6.34-6.36 (1H, m), 6.11 (1H, t, J=2.1 Hz), 5.76 (1H, s), 3.67-3.73 (4H, m), 2.96-3.01 (4H, m), 2.20 (3H, s), 1.93 (3H, s). Mass Spectrum (ESI) m/e=472.1 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica; 0-5% methanol in DCM)

Sources & evidence

ORD record
ord-f63a396e44d44b0ab15e5bca69e25f23
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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