Methyl 2-[5-[(4-cyanophenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylate → 2-[5-[(4-Cyanophenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylic acid

HRID 878604Notes

Reaction equation

HRID 878604 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1)#[N:2]>C(#N)C.O>[C:1]([C:3]1[CH:8]=[CH:7][C:6]([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:5][CH:4]=1)#[N:2]

Participants

3

Reactant 1

HCID 86725567Methyl 2-[5-[(4-cyanophenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylate

Product 1

HCID 867255682-[5-[(4-Cyanophenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylic acid

Reagents, catalysts & solvents 1

HCID 18373917Acetonitrile--water (1/1)Solvent

Procedure

The title compound was prepared from methyl 2-[5-[(4-cyanophenyl)methoxy]pyrazol-1-yl]pyridine-4-carboxylate (EXAMPLE 98) according to the procedure for the preparation of Example 97, part B. 1H NMR (400 MHz, DMSO-d6): δ 5.41 (2H, s), 6.00 (1H, d, J=2.0 Hz), 7.61 (1H, d, J=1.6 Hz), 7.67-7.69 (2H, m), 7.77 (1H, dd, J=0.8 Hz, J=4.8 Hz), 7.87-7.89 (2H, m), 8.10 (1H, s), 8.70 (1H, d, J=5.2 Hz), 13.92 (1H, s). LCMS (mobile phase: 10%-95% Acetonitrile-Water-0.02% NH4Ac): purity is >95%, Rt=2.104 min. [M+H] Calc'd for C17H12N4O3, 321; Found, 321.

Workup

  1. customaccording to the procedure for the preparation of Example 97, part B

Sources & evidence

ORD record
ord-0a2d39002632467eab0cac856c4aa0db
Source dataset
uspto-grants-2015_03
Patent number
US08987461B2

Reaction notes

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