Hydrochloric Acid → 1-[(4-Fluorophenyl)methyl]pyrazolo[3,4-c]pyridine-5-carbohydroxamic acid

HRID 2377071Notes

Reaction equation

HRID 2377071 reaction equation
[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16](OC)=[O:17])[CH:15]=[C:10]3[CH:9]=[N:8]2)=[CH:4][CH:3]=1.[NH2:22][OH:23].[OH-].[Na+].Cl>CO.O>[F:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][N:7]2[C:11]3=[CH:12][N:13]=[C:14]([C:16]([NH:22][OH:23])=[O:17])[CH:15]=[C:10]3[CH:9]=[N:8]2)=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 14798Sodium HydroxideHCID 691988241h-Pyrazolo[3,4-c]pyridine-5-carboxylic acid,1-[(4-fluorophenyl)methyl]-,methyl ester

Product 1

HCID 1354294271-[(4-Fluorophenyl)methyl]pyrazolo[3,4-c]pyridine-5-carbohydroxamic acidYield 52%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent3×

Procedure

To a stirring solution of methyl 1-(4-fluorobenzyl)-1H-pyrazolo[3,4-c]pyridine-5-carboxylate (96 mg, 0.33 mmol) in methanol (4 mL) was added a 50% v/v solution of hydroxylamine in water (2 mL) followed by 10% sodium hydroxide solution in water (1 mL). The mixture was stirred for 2 hours, then 10% hydrochloric acid solution in water (1 mL) was added until a neutral pH was obtained, and the mixture was concentrated under reduced pressure. Methanol was added and the mixture was purified by reverse phase preparative HPLC (Dionex, 0-40% acetonitrile:water v/v, 40 minutes) to provide a white solid (50 mg, 52% yield). 1H NMR (DMSO-d6): δ ppm 9.22 (s, 1H), 8.39 (s, 1H), 8.37 (s, 1H), 7.37 (m, 2H), 7.15 (m, 2H), 5.83 (s, 2H). Anal. HPLC: >95% (@ 254, 222 nM). HRMS calcd for C14H11FN4O2 (M+H) 287.0939, found 287.0936.

Workup

  1. customwas obtained
  2. concentrationthe mixture was concentrated under reduced pressure
  3. additionMethanol was added
  4. customthe mixture was purified by reverse phase preparative HPLC (Dionex, 0-40% acetonitrile:water v/v, 40 minutes)

Sources & evidence

ORD record
ord-d1ca50ce7da54e31ac4cc79a150af571
Source dataset
uspto-grants-2008_12
Patent number
US07468375B2

Reaction notes

Loading…