Triethylamine → HCID 117987751, compound

HRID 2206225Notes

Reaction equation

CS(O[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([C:13]2[C:17]3[C:18]([O:22][CH3:23])=[N:19][CH:20]=[CH:21][C:16]=3[N:15]([C:24]3[C:29]([F:30])=[CH:28][CH:27]=[CH:26][C:25]=3[F:31])[N:14]=2)[CH:8]=1)(=O)=O.[NH:32]1[CH2:36][CH2:35][CH2:34][CH2:33]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>CN(C=O)C>[F:31][C:25]1[CH:26]=[CH:27][CH:28]=[C:29]([F:30])[C:24]=1[N:15]1[C:16]2[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH3:23])[C:17]=2[C:13]([C:9]2[CH:10]=[CH:11][CH:12]=[C:7]([CH2:6][N:32]3[CH2:36][CH2:35][CH2:34][CH2:33]3)[CH:8]=2)=[N:14]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 3-(1-(2,6-difluorophenyl)-4-methoxy-1H-pyrazolo[4,3-c]pyridin-3-yl)benzyl methanesulfonate (100 mg) obtained in Step B of Example 258 and pyrrolidine (0.028 mL) in DMF (3 mL) was added triethylamine (0.047 mL) at room temperature, and the mixture was stirred at 60° C. for 4 hr. To the reaction mixture was added saturated aqueous sodium hydrogencarbonate solution, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane) to give the title compound (70 mg).

Workup

extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed successively with water and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane)

Sources & evidence

ORD record: ord-3596e43c333a47d686be0984cff24cea
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09371320B2

Reaction notes

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