Ethanol → 2-[4-[2-[(4-Fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carboxylic acid

HRID 514559Notes

Reaction equation

HRID 514559 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:25])[CH2:10][CH2:11][C:12]2[CH:13]=[N:14][N:15]([C:17]3[CH:22]=C(C#N)[CH:20]=[CH:19][N:18]=3)[CH:16]=2)=[CH:4][CH:3]=1.[OH-:26].[Na+].[CH2:28]([OH:30])[CH3:29]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][N:9]([CH3:25])[CH2:10][CH2:11][C:12]2[CH:13]=[N:14][N:15]([C:17]3[CH:22]=[C:29]([C:28]([OH:26])=[O:30])[CH:20]=[CH:19][N:18]=3)[CH:16]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 867256642-[4-[2-[(4-Fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carbonitrile

Product 1

HCID 867256662-[4-[2-[(4-Fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carboxylic acidYield 80%

Procedure

Charged 2-[4-[2-[(4-fluorophenyl)methyl-methylamino]ethyl]pyrazol-1-yl]pyridine-4-carbonitrile (270 mg, 0.8 mmol), NaOH aqueous (5M, 0.5 mL) and ethanol (10 mL) to a flask, the mixture was then heated to reflux for half an hour, cooled in an ice-water bath, adjusted PH to 3˜4, filtered, collected the solid and dried to give the title compound (226 mg, 80%). 1H NMR (400 MHz, DMSO-d6): 2.70 (3H, s), 3.01-3.06 (2H, m), 3.25-3.27 (1H, m), 3.31-3.39 (1H, m), 4.26-4.30 (1H, m), 4.44-4.48 (1H, m), 7.29-7.34 (2H, m), 7.64-7.68 (2H, m), 7.74-7.76 (1H, m), 7.81 (1H, s), 8.28 (1H, s), 8.61 (s, 1H), 8.64 (1H, J=5.2 Hz, d), 10.49 (1H, br). [M+H] Calc'd for C19H19FN4O2, 355. Found, 355.

Workup

  1. temperaturethe mixture was then heated
  2. temperatureto reflux for half an hour
  3. temperaturecooled in an ice-water bath
  4. filtrationfiltered
  5. customcollected the solid
  6. customdried

Sources & evidence

ORD record
ord-c5adaddb7d5e40bb84d36fcfb8bc4746
Source dataset
uspto-grants-2015_08
Patent number
US09107916B2

Reaction notes

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