Lithium hydroxide, monohydrate → 2-[5-[(3-Cyanophenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylic acid

HRID 514445Notes

Reaction equation

HRID 514445 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][O:10][C:11]2[N:15]([C:16]3[CH:21]=[C:20]([C:22]([O:24]C)=[O:23])[CH:19]=[CH:18][N:17]=3)[N:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].O[Li].O>O.C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([CH2:9][O:10][C:11]2[N:15]([C:16]3[CH:21]=[C:20]([C:22]([OH:24])=[O:23])[CH:19]=[CH:18][N:17]=3)[N:14]=[CH:13][CH:12]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86725565Methyl 2-[5-[(3-cyanophenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylate

Product 1

HCID 867255662-[5-[(3-Cyanophenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8028TetrahydrofuranSolvent

Procedure

A solution of methyl 2-[5-[(3-cyanophenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylate (1.0 eq) and LiOH.H2O (3.0 eq) in a mixture of water (2 mL) and THF (2 mL) was stirred at room temperature for 30 min. Diluted with another 2 mL water, and the mixture was washed with ethyl acetate twice (6 mL×2). The water phase was acidified with 1N HCl (pH=3), filtered and dried the solid to give the title compound. 1H NMR (400 MHz, DMSO-d6): δ 5.36 (2H, s), 6.03 (1H, s), 7.61-7.64 (2H, m), 7.77-7.78 (1H, m), 7.82-7.84 (2H, m), 7.96 (1H, s), 8.09 (1H, s), 8.69 (1H, d, J=4.4 Hz), 13.92 (1H, s). LCMS (mobile phase: 10%-95% Acetonitrile-Water-0.02% NH4Ac): purity is >95%, Rt=2.106 min. [M+H] Calc'd for C17H12N4O3, 321. Found, 321.

Workup

  1. washthe mixture was washed with ethyl acetate twice (6 mL×2)
  2. filtrationfiltered
  3. customdried the solid

Sources & evidence

ORD record
ord-d9e7ff53d5f647d29dae65a2abfbf57f
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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