HCID 67958117, compound → 5-Chloro-2-(3-((4-fluoro-2-methylphenyl)(methyl)amino)azetidin-1-yl)nicotinic acid

HRID 72469Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([N:16]([CH3:25])[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]>O1CCOCC1.O>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:13][CH:14]([N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])[CH3:25])[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-chloro-2-(3-(methyl(2-methyl-4-fluoro-phenyl)amino)azetidin-1-yl)nicotinate (D87) (170 mg, 0.467 mmol) in 1,4 dioxane (3 ml) and water (1 ml) 1M NaOH (0.7 ml) was added. The mixture was stirred at 60° C. for 2 h. Organic solvent was evaporated and remaining aqueous were acidified 2N HCl and extracted with ethylacetate (3×5 ml). The combined organic phases after solvent evaporation afforded the title compound (D120) (156 mg)

Workup

customOrganic solvent was evaporated
extractionextracted with ethylacetate (3×5 ml)
customThe combined organic phases after solvent evaporation

Sources & evidence

ORD record: ord-9cff42a459994195a81ab7ec4f0cee71
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08828987B2

Reaction notes

Loading…