Hydrochloric Acid → N-(4-((2-(1H-pyrazol-4-yl)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide hydrochloride

HRID 1472621Notes

Reaction equation

HRID 1472621 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([O:12][C:13]3[C:18]([F:19])=[CH:17][C:16]([NH:20][C:21]([C:23]4[C:24](=[O:39])[N:25]([C:32]5[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=5)[CH:26]=[CH:27][C:28]=4[O:29][CH2:30][CH3:31])=[O:22])=[C:15]([F:40])[CH:14]=3)[CH:9]=[CH:8][N:7]=2)[CH:3]=[N:2]1.[ClH:41].CCOCC>CC#N>[ClH:41].[NH:1]1[CH:5]=[C:4]([C:6]2[CH:11]=[C:10]([O:12][C:13]3[C:18]([F:19])=[CH:17][C:16]([NH:20][C:21]([C:23]4[C:24](=[O:39])[N:25]([C:32]5[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=5)[CH:26]=[CH:27][C:28]=4[O:29][CH2:30][CH3:31])=[O:22])=[C:15]([F:40])[CH:14]=3)[CH:9]=[CH:8][N:7]=2)[CH:3]=[N:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 86270235HCID 86270235, compound

Product 1

HCID 90426596N-(4-((2-(1H-pyrazol-4-yl)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide hydrochlorideYield 87.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a mixture of N-(4-((2-(1H-pyrazol-4-yl)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide (87 mg, 0.159 mmol) in MeCN (3 mL) was added 0.1 N HCl (1.59 mL, 0.159 mmol) and the solution frozen and lyophilized. The material was treated with Et2O, the solid collected via filtration and dried to afford N-(4-((2-(1H-pyrazol-4-yl)pyridin-4-yl)oxy)-2,5-difluorophenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide hydrochloride (81 mg, 79%) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 11.28 (s, 1H), 8.54-8.37 (m, 4H), 7.93 (d, J=7.8 Hz, 1H), 7.67 (s, 1H), 7.60 (m, 1H), 7.48 (m, 2H), 7.37 (m, 2H), 7.04 (s, 1H), 6.56 (d, J=6.7 Hz, 1H), 4.28 (q, J=6.9 Hz, 2H), 1.33 (t, J=7.0 Hz, 3H); MS (ESI) m/z: 548.2 (M+H+).

Workup

  1. temperaturethe solution frozen
  2. filtrationthe solid collected via filtration
  3. customdried

Sources & evidence

ORD record
ord-fc2048062e214573b8c9b3820e8849fd
Source dataset
uspto-grants-2015_04
Patent number
US09012635B2

Reaction notes

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