Sodium Hydroxide → 5-Fluoro-2-(3-((4-fluoro-2-methylphenyl)amino)azetidin-1-yl)nicotinic acid

HRID 72484Notes

Reaction equation

[F:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+]>O1CCOCC1.O>[F:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:13][CH:14]([NH:16][C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH2:15]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of methyl 5-fluoro-2-(3-((4-fluoro-2-methylphenyl)amino)azetidin-1-yl)nicotinate (D90) (150 mg, 0.450 mmol) in 1,4-dioxane/water (3 ml/1 ml), 1M NaOH (0.675 ml, 0.657 mmol) was added and the resulting mixture was stirred 2 h at 60° C. Organic solvent was evaporated. The remaining aqueous were washed with dichloromethane (5 ml) then acidified to pH2 by addition of 2M HCl and extracted with ethylacetate (3×20 ml). Collected organics, after solvent evaporation afforded the title compound (D135) (140 mg).

Workup

customOrganic solvent was evaporated
washThe remaining aqueous were washed with dichloromethane (5 ml)
additionthen acidified to pH2 by addition of 2M HCl
extractionextracted with ethylacetate (3×20 ml)
customCollected organics, after solvent evaporation

Sources & evidence

ORD record: ord-6ac1b0b128a04874a890d135fbd1aa6a
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Reaction notes

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