Tetrahydrofuran → 5-(5-Chloro-2-(((4'-chloro-[1,1'-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinic acid

HRID 405140Notes

Reaction equation

HRID 405140 reaction equation
[OH-].[Na+].C1COCC1.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:25][N:26]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)=[CH:30][CH:29]=2)[CH3:27])=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([O:23]C)=[O:22])=[N:19][CH:20]=2)[CH:14]=1>CO>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:25][N:26]([C:28]2[CH:33]=[CH:32][C:31]([C:34]3[CH:35]=[CH:36][C:37]([Cl:40])=[CH:38][CH:39]=3)=[CH:30][CH:29]=2)[CH3:27])=[C:13]([C:15]2[CH:16]=[CH:17][C:18]([C:21]([OH:23])=[O:22])=[N:19][CH:20]=2)[CH:14]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71059984Methyl 5-(5-chloro-2-(((4'-chloro-[1,1'-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinate

Product 1

HCID 710601375-(5-Chloro-2-(((4'-chloro-[1,1'-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinic acid

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A 3M aqueous solution of NaOH (0.47 mL, 1.42 mmol) was added to a THF (2 mL) and MeOH (1 mL) solution of methyl 5-(5-chloro-2-(((4′-chloro-[1,1′-biphenyl]-4-yl)(methyl)amino)methyl)phenyl)picolinate (226 mg, 0.47 mmol) and the resulting homogeneous mixture was stirred at room temperature. After 16 h the resulting mixture was concentrated in vacuo, suspended in water, and acidified with 2 M HCl. The resulting precipitate was filtered off and dried in vacuo to yield the title compound.

Workup

  1. concentrationAfter 16 h the resulting mixture was concentrated in vacuo
  2. filtrationThe resulting precipitate was filtered off
  3. customdried in vacuo

Sources & evidence

ORD record
ord-af3c55ec236f4c8ba7067599458c906b
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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