Hydrochloric Acid → HCID 71253637, compound

HRID 1774998Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:18]2[C:13](=[CH:14][N:15]=[C:16]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)[CH:17]=2)[N:12](C2CCCCO2)[N:11]=1.Cl>CO.O>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[C:18]2[C:13](=[CH:14][N:15]=[C:16]([C:19]3[CH:20]=[N:21][N:22]([CH3:24])[CH:23]=3)[CH:17]=2)[NH:12][N:11]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a stirred mixture of 3-(2-fluoro-5-methoxyphenyl)-5-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine (37.0 mg, 0.09 mmol) in methanol (5.0 mL) was added 6 M HCl in water (0.66 mL). The reaction mixture was stirred at 60° C. for 3 days. Volatile solvent was evaporated in vacuo, and the crude was diluted into ethyl acetate (˜30 mL). The organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Trituration from ether-heptanes afforded 172 as a solid (15.3 mg, 52.1%). 1H NMR (400 MHz, DMSO) δ 13.88 (s, 1H), 9.06 (s, 1H), 8.25 (s, 1H), 7.97 (s, 1H), 7.88 (s, 1H), 7.36 (t, J=9.6 Hz, 1H), 7.31 (dd, J=5.7, 3.2 Hz, 1H), 7.09 (s, 1H), 3.88 (s, 3H), 3.83 (s, 3H). LC/MS: m/z 324.0 [M+1]

Workup

customVolatile solvent was evaporated in vacuo
additionthe crude was diluted into ethyl acetate (˜30 mL)
washThe organic layer was washed with saturated aqueous sodium bicarbonate solution, water and brine
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-349faad692334e029dd0207d25f165a5
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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