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Hydrochloric Acid → 5-Chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1-yl)nicotinic acid

HRID 72468
Notes
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Reaction equation

HRID 72468 reaction equation
[Cl: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[F:24])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([O:9]C)=[O:8].[OH-].[Na+].Cl>O1CCOCC1.O>[Cl: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[F:24])[CH2:13]2)=[C:6]([CH:11]=1)[C:7]([OH:9])=[O:8]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67958025Methyl 5-chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1-yl)nicotinate

Product 1

HCID 679580805-Chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1-yl)nicotinic acidYield 99.1%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)
Solvent

Conditions

Temperature
60 °C

Procedure

To a solution of methyl 5-chloro-2-(3-((2,4-difluorophenyl)amino)azetidin-1-yl)nicotinate (D85) (37 mg, 0.104 mmol) in a mixture 3:1 1,4-dioxane/water (4 ml), 1M NaOH (0.157 ml) was added and the resulting mixture was stirred 12 h at 60° C. After cooling the reaction mixture was acidified to pH 1 by addition of 1M HCl. The resulting precipitate was collected by filtration and afforded the title compound (D118) (35 mg).

Workup

  1. temperatureAfter cooling the reaction mixture
  2. filtrationThe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-eb0af1be355f463fbbdc1ec65a21a03d
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08828987B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes