Tetrahydrofuran → 2-{[3-cyclopentyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzoic acid

HRID 915582Notes

Reaction equation

HRID 915582 reaction equation
[CH:1]1([C:6]2[CH:10]=[C:9]([NH:11][C:12]3[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=3[C:14]([O:16]C)=[O:15])[N:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[N:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C1COCC1.[OH-].[Na+]>CO>[CH:1]1([C:6]2[CH:10]=[C:9]([NH:11][C:12]3[CH:21]=[CH:20][CH:19]=[CH:18][C:13]=3[C:14]([OH:16])=[O:15])[N:8]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[CH3:28])[N:7]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 58958591HCID 58958591, compound

Product 1

HCID 589585922-{[3-cyclopentyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzoic acidYield 79.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of methyl 2-{[3-cyclopentyl-1-(2-methylphenyl)-1H-pyrazol-5-yl]amino}benzoate (0.59 mmol, 220 mg) in MeOH (1.8 mL) was added THF (5.4 mL) and 1N aqueous NaOH (1.8 mL). The reaction was stirred at rt for 21 h. The organic solvents were removed under reduced pressure, the residue was diluted with water, and the aqueous solution extracted with diethylether (2×5 mL). The aqueous layer was acidified to pH=1 to 2 with 1N aqueous HCl. The mixture was extracted with ethyl acetate (3×5 mL). After removal of the solvent under reduced pressure, the product was obtained as a white solid (169 mg, 79%). 1H NMR (400 MHz, DMSO-d6) δ 1.58-1.62 (m, 2H), 1.65-1.78 (m, 4H), 1.90-2.01 (m, 2H), 2.06 (s, 3H), 2.99-3.10 (m, 1H), 6.23 (s, 1H), 6.80 (t, 1H), 7.20-7.30 (m, 3H), 7.30-7.40 (m, 2H), 7.42-7.51 (m, 1H), 7.81 (d, 1H), 9.84 (s, 1H), 13.14 (s, 1H). ES-MS m/z 362.3 (MH+), HPLC RT (min) 3.39.

Workup

  1. customThe organic solvents were removed under reduced pressure
  2. additionthe residue was diluted with water
  3. extractionthe aqueous solution extracted with diethylether (2×5 mL)
  4. extractionThe mixture was extracted with ethyl acetate (3×5 mL)
  5. customAfter removal of the solvent under reduced pressure

Sources & evidence

ORD record
ord-77d6c9caf05e437d8681d767a53b97a5
Source dataset
uspto-grants-2007_09
Patent number
US07265144B2

Reaction notes

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