Sodium Hydroxide → 4-[({[5-Fluoro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)methyl]benzoic acid

HRID 1293162Notes

Reaction equation

HRID 1293162 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26]C)=[O:25])=[CH:22][CH:21]=2)=[O:17])[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.[OH-].[Na+]>CO>[F:1][C:2]1[CH:3]=[C:4]([C:16]([NH:18][CH2:19][C:20]2[CH:21]=[CH:22][C:23]([C:24]([OH:26])=[O:25])=[CH:28][CH:29]=2)=[O:17])[C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 57572271HCID 57572271, compound

Product 1

HCID 589053584-[({[5-Fluoro-2-(4-fluorophenoxy)pyridin-3-YL]carbonyl}amino)methyl]benzoic acidYield 64%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of methyl 4-[({[5-fluoro-2-(4-fluorophenoxy)pyridin-3-yl]carbonyl}amino)methyl]benzoate (step 3, 407 mg, 1.02 mmol) in methanol (10 ml)_was added 2 N sodium hydroxide aqueous solution (2 mL). The reaction mixture was stirred at room temperature for 3 h and then evaporated. The residue was partitioned between ethyl acetate (100 mL) and 2 N hydrochloric acid (100 mL). The organic phase was separated and the aqueous phase was extracted with ethyl acetate (100 mL). The combined organic extracts were washed with brine (50 mL), dried (sodium_sulfate), and concentrated. The residual solids were recrystallized from ethyl acetate to afford 248 mg (64%) of the title compound as white solids: 1H-NMR (CDCl3) δ 8.40 (1H, dd, J=8.3, 3.1 Hz), 8.30 (1H, br.s), 8.09–8.04 (3H, m), 7.45 (2H, d, J=8.1 Hz), 7.17–7.06 (4H, m), 4.79 (2H, d, J=5.9 Hz); MS (EI) m/z 384 (M+), (ESI) m/z 385 (M+H)+, 383 (M−H)−.

Workup

  1. customevaporated
  2. customThe residue was partitioned between ethyl acetate (100 mL) and 2 N hydrochloric acid (100 mL)
  3. customThe organic phase was separated
  4. extractionthe aqueous phase was extracted with ethyl acetate (100 mL)
  5. washThe combined organic extracts were washed with brine (50 mL)
  6. dry with materialdried (sodium_sulfate)
  7. concentrationconcentrated
  8. customThe residual solids were recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-eeec290c7ae448adbf2d6c96ee46b701
Source dataset
uspto-grants-2007_07
Patent number
US07238714B2

Reaction notes

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