Thionyl Chloride → HCID 86604679, compound

HRID 130495Notes

Reaction equation

HRID 130495 reaction equation
[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11]3[C:14]([C:28]([F:31])([F:30])[F:29])=[N:15][N:16]([C:17]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:18]=4[C:19](O)=[O:20])[C:10]=3[C:9]2=[O:32])=[CH:4][CH:3]=1.S(Cl)([Cl:35])=O>C(Cl)(Cl)Cl>[I:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:13][CH2:12][C:11]3[C:14]([C:28]([F:31])([F:30])[F:29])=[N:15][N:16]([C:17]4[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][C:18]=4[C:19]([Cl:35])=[O:20])[C:10]=3[C:9]2=[O:32])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 693098972-[6-(4-Iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid

Product 1

HCID 86604679HCID 86604679, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-[6-(4-Iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoic acid (186 mg, 0.334 mmol) was dissolved in dry chloroform (10 mL) to which was added thionyl chloride (243 μL, 3.34 mmol), and the reaction heated to reflux. The solvent was evaporated, and the residue dried under vacuum to give 2-[6-(4-iodo-phenyl)-7-oxo-3-trifluoromethyl-4,5,6,7-tetrahydro-pyrazolo[3,4-c]pyridin-1-yl]-5-methoxy-benzoyl chloride as a pale yellow foam. This material was dissolved in dry methylene chloride (10 mL) to which were added pyridine (0.14 mL, 1.67 mmol), N,N-dimethylaminopyridine (4 mg, 0.033 mmol), and lastly C-(1H-imidazol-2-yl)-methylamine bis-hydrochloride (114 mg, 0.668 mmol). Upon completion of the reaction the solvent was evaporated, and the residue was purified by preparative HPLC to give the title compound (69 mg, 24%) as a colorless solid. MS (ES+) 636.9 (M+H)+(100%).

Workup

  1. temperaturethe reaction heated to reflux
  2. customThe solvent was evaporated
  3. customthe residue dried under vacuum

Sources & evidence

ORD record
ord-278500dc088e429f9b560ee9a02d513b
Source dataset
uspto-grants-2008_06
Patent number
US07381732B2

Reaction notes

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