Tetrahydrofuran → 5-(2-(4-Methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinic acid

HRID 923554Notes

Reaction equation

HRID 923554 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([O:21]C)=[O:20])=[N:17][CH:18]=2)=[O:11])=[C:5]([C:23]([F:26])([F:25])[F:24])[CH:4]=1.C1COCC1.[OH-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([C:19]([OH:21])=[O:20])=[N:17][CH:18]=2)=[O:11])=[C:5]([C:23]([F:25])([F:26])[F:24])[CH:4]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 71076831Methyl 5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinate

Product 1

HCID 710766575-(2-(4-Methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinic acidYield 67%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Prepared using General Procedure 9: To a stirred solution of methyl 5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinate INT-14 (74 mg, 0.2 mmol) in MeOH (1 mL) and THF (4 mL) was added 2 N NaOH (1 mL). The reaction mixture was stirred at room temperature overnight then concentrated. The residue was diluted with water (1 mL) and acidified with 1 N HCl to a pH of 2. The resulting precipitate was isolated by filtration and the filter cake was washed with water. Crude product was dried under vacuum to afford 48 mg (67%) of 5-(2-(4-methoxy-2-(trifluoromethyl)phenyl)acetamido)picolinic acid INT-15 which was used in the next step without purification. LCMS-ESI (m/z) calculated C16H13F3N2O4: 354; found 355, tR=2.66 min (Method 1). 1H NMR (400 MHz, DMSO) δ 10.71 (s, 1H), 8.83 (d, J=2.2 Hz, 1H), 8.18 (dd, J=8.6, 2.5 Hz, 1H), 8.02 (d, J=8.6 Hz, 1H), 7.46 (d, J=8.5 Hz, 1H), 7.29-7.10 (m, 2H), 3.92 (s, 2H), 3.82 (d, J=5.3 Hz, 3H), 3.35 (s, 1H).

Workup

  1. customPrepared
  2. concentrationthen concentrated
  3. additionThe residue was diluted with water (1 mL)
  4. customThe resulting precipitate was isolated by filtration
  5. washthe filter cake was washed with water
  6. customCrude product was dried under vacuum

Sources & evidence

ORD record
ord-85b232480e754824a8947fc7ebb0380e
Source dataset
uspto-grants-2016_03
Patent number
US09278910B2

Reaction notes

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