Sodium Hydroxide → 4-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid

HRID 917785Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:11]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([C:19]#[CH:20])=[CH:15][C:14]=2[F:21])=[CH:10][C:9](=[O:22])[N:8]([CH3:23])[CH:7]=1)=[O:5])C.[OH-].[Na+]>CCO>[C:19]([C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:11]2[C:6]([C:4]([OH:5])=[O:3])=[CH:7][N:8]([CH3:23])[C:9](=[O:22])[CH:10]=2)=[C:14]([F:21])[CH:15]=1)#[CH:20]

Participants

Conditions

Temperature: 70 °C

Procedure

4-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid ethyl ester (0.67 mg, 2.13 mmol) was suspended in EtOH (20 mL), to which was added NaOH (0.26 g, 6.40 mmol). This mixture was stirred at 70° C. for 1 hour. The solvent was removed under reduced pressure. The residue was acidified with 1N HCl then the resulting precipitate was filtered and washed with water. The tan solid was dried under high vacuum pump to afford 4-(4-Ethynyl-2-fluoro-phenylamino)-1-methyl-6-oxo-1,6-dihydro-pyridine-3-carboxylic acid (0.56 g, 91%). 1H NMR [(CD3)2SO, 400 MHz] δ 13.31 (v br s, 1H), 9.79 (s, 1H), 8.51 (s, 1H), 7.49 (dd, J=10.1, 1.9 Hz, 1H), 7.44 (dd, J=8.4, 1.7, 0.8 Hz, 1H), 7.32 (dd, J=8.5 Hz, 1H), 5.61 (dd, J=0.7 Hz, 1H), 4.25 (s, 1H), 3.41 (s, 3H). Anal. Calcd for C15H11FIN2O3: C, 62.94; H, 3.87; N, 9.79. Found: C, 62.56; H, 3.78; N, 9.30.

Workup

customThe solvent was removed under reduced pressure
filtrationthe resulting precipitate was filtered
washwashed with water
customThe tan solid was dried under high vacuum pump

Sources & evidence

ORD record: ord-64eea8d63ca345ea9c01cd4496dea62d
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273877B2

Reaction notes

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