Sodium Hydroxide → 3-{1-[(6-Chloropyrazin-2-yl)amino]ethyl}benzoic acid

HRID 1255836Notes

Reaction equation

HRID 1255836 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([O:16]C)=[O:15])[CH3:10])[CH:5]=[N:4][CH:3]=1.[OH-].[Na+]>CO.ClCCl>[Cl:1][C:2]1[N:7]=[C:6]([NH:8][CH:9]([C:11]2[CH:12]=[C:13]([CH:18]=[CH:19][CH:20]=2)[C:14]([OH:16])=[O:15])[CH3:10])[CH:5]=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86641858Methyl 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoate

Product 1

HCID 866418593-{1-[(6-Chloropyrazin-2-yl)amino]ethyl}benzoic acidYield 41%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of methyl 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoate (30 mg, 0.1 mmol) in dilute aqueous sodium hydroxide (0.5 mL, 2M, 1 mmol), methanol (2 mL) and dichloromethane (1 mL) was stirred at room temperature for 16 hours. After this time the mixture was concentrated under reduced pressure and the residue was dissolved in water (5 mL) which was then acidified to pH 6 with dilute aqueous hydrochloric acid (1M). The aqueous solution was extracted with ethyl acetate (3×10 mL) and the extracts were washed with brine (10 mL), dried (MgSO4) and concentrated under reduced pressure to give 3-{1-[(6-chloropyrazin-2-yl)amino]ethyl}benzoic acid (11 mg, 41%) as a beige coloured oil.

Workup

  1. concentrationAfter this time the mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water (5 mL) which
  3. extractionThe aqueous solution was extracted with ethyl acetate (3×10 mL)
  4. washthe extracts were washed with brine (10 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-fb086155d60a48f8800961d82b34f110
Source dataset
uspto-grants-2013_06
Patent number
US08461161B2

Reaction notes

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