Potassium Carbonate → HCID 59631192, compound

HRID 1431783Notes

Reaction equation

HRID 1431783 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]([CH:70]2[CH2:72][CH2:71]2)=[O: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]([CH:70]4[CH2:71][CH2:72]4)=[O: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 59631247HCID 59631247, compound

Product 1

HCID 59631192HCID 59631192, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6386tert-ButanolSolvent

Procedure

Prepared according to Procedure X by stirring palladium (II) acetate (1.1 mg, 4.78 μmol), XPhos (6.8 mg, 0.014 mmol), 4-chloro-7-fluoro-3-methyl-2-(pyridin-2-yl)quinoline (0.026 g, 0.096 mmol), N-(3-amino-5-morpholinophenyl)cyclopropanecarboxamide (0.025 g, 0.096 mmol), potassium carbonate (0.033 g, 0.239 mmol), and tert-butanol (1 mL) at 110° C. for 1 hour. Purification by column chromatography (silica; 0-10% methanol in DCM) afforded N-(3-((7-fluoro-3-methyl-2-(2-pyridinyl)-4-quinolinyl)amino)-5-(4-morpholinyl)phenyl)cyclopropanecarboxamide as a yellow amorphous solid. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 8.68 (1H, d, J=4.3 Hz), 8.26 (1H, br. s.), 7.86 (2H, td, J=7.7, 1.7 Hz), 7.74 (1H, d, J=7.0 Hz), 7.62 (1H, dd, J=10.0, 2.0 Hz), 7.33-7.42 (1H, m), 7.24 (1H, br. s.), 7.14-7.21 (1H, m), 6.15 (2H, br. s.), 6.02 (1H, br. s.), 3.69-3.87 (4H, m), 3.05-3.20 (4H, m), 2.29 (3H, s), 1.27 (1H, t, J=7.1 Hz), 0.92-0.99 (2H, m), 0.57-0.73 (2H, m). Mass Spectrum (ESI) m/e=498.2 (M+1).

Workup

  1. customPrepared
  2. customPurification by column chromatography (silica; 0-10% methanol in DCM)

Sources & evidence

ORD record
ord-a8fc020dab59433a8d52056e2c48286c
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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