Hydrochloric Acid → 5-(1-methyl-1H-pyrazol-4-yl)-3-phenyl-1H-pyrazolo[3,4-c]pyridine

HRID 1774974Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=4)=[N:14][N:13](C4CCCCO4)[C:10]3=[CH:11][N:12]=2)[CH:4]=[N:3]1.Cl>CO.O>[CH3:1][N:2]1[CH:6]=[C:5]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=4)=[N:14][NH:13][C:10]3=[CH:11][N:12]=2)[CH:4]=[N:3]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred solution of 5-(1-methyl-1H-pyrazol-4-yl)-3-phenyl-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (54.5 mg, 0.152 mmol) in MeOH (8 mL) was added 6 M HCl in water. The reaction mixture was stirred at 60° C. under N2 for 16 h. The reaction mixture was cooled to room temperature. Volatile solvent was removed under reduced pressure. The crude was redissolved in EtOAc. The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine, dried over Na2SO4, filtered, and evaporated in vacuo. Crystallization from DCM-heptanes afforded 133 as a solid (40 mg, 95.8%). 1H NMR (400 MHz, DMSO) δ 13.71 (broad s, 1H), 9.04 (s, 1H), 8.32 (s, 1H), 8.24 (s, 1H), 8.09 (d, J=7.3 Hz, 3H), 7.55 (t, J=7.5 Hz, 2H), 7.44 (t, J=7.4 Hz, 1H), 3.90 (s, 3H). LC/MS: m/z 276.1 [M+1]

Workup

temperatureThe reaction mixture was cooled to room temperature
customVolatile solvent was removed under reduced pressure
dissolutionThe crude was redissolved in EtOAc
washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
dry with materialdried over Na2SO4
filtrationfiltered
customevaporated in vacuo
customCrystallization from DCM-heptanes

Sources & evidence

ORD record: ord-9c3f8fe25bf14320acdf8fdb2fcfeb03
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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