3-Fluoroaniline → 5-Chloro-2-(3-((3-fluorophenyl)amino)azetidin-1-yl)nicotinic acid

HRID 72467Notes

Reaction equation

HRID 72467 reaction equation
[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14](OS(C)(=O)=O)[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[F:21][C:22]1[CH:23]=[C:24]([CH:26]=[CH:27][CH:28]=1)[NH2:25]>>[Cl:1][C:2]1[CH:3]=[N:4][C:5]([N:12]2[CH2:15][CH:14]([NH:25][C:24]3[CH:26]=[CH:27][CH:28]=[C:22]([F:21])[CH:23]=3)[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]

Participants

3

Reactant 2

HCID 97423-FluoroanilineHCID 86697874Methyl 5-chloro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate

Product 1

HCID 679581015-Chloro-2-(3-((3-fluorophenyl)amino)azetidin-1-yl)nicotinic acidYield 33.2%

Procedure

The title compound (D116) (40 mg) was prepared according to the experimental procedure described in Description 115 starting from methyl 5-chloro-2-(3-((methylsulfonyl)oxy)azetidin-1-yl)nicotinate (D63) (120 mg, 0.374 mmol) and 3-Fluoroaniline (0.036 ml, 0.374 mmole).

Sources & evidence

ORD record
ord-ceca98f8efd74ece85f4fe9fa8fdb09c
Source dataset
uspto-grants-2014_09
Patent number
US08828987B2

Reaction notes

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