Hydrochloric Acid → 2-(3,5-Bis-trifluoromethyl-phenyl)-N-[4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-N-methyl-isobutyramide

HRID 451219Notes

Reaction equation

C([N:8]1[C:12]2=[N:13][CH:14]=[C:15]([N:25]([CH3:45])[C:26](=[O:44])[C:27]([C:30]3[CH:35]=[C:34]([C:36]([F:39])([F:38])[F:37])[CH:33]=[C:32]([C:40]([F:43])([F:42])[F:41])[CH:31]=3)([CH3:29])[CH3:28])[C:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])=[C:11]2[CH:10]=[N:9]1)C1C=CC=CC=1.Cl>CO.[Pd]>[F:43][C:40]([F:41])([F:42])[C:32]1[CH:31]=[C:30]([C:27]([CH3:29])([CH3:28])[C:26]([N:25]([C:15]2[C:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][C:18]=3[CH3:24])=[C:11]3[CH:10]=[N:9][NH:8][C:12]3=[N:13][CH:14]=2)[CH3:45])=[O:44])[CH:35]=[C:34]([C:36]([F:37])([F:38])[F:39])[CH:33]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of N-[1-benzyl-4-(4-fluoro-2-methyl-phenyl)-1H-pyrazolo[3,4-b]pyridin-5-yl]-2-(3,5-bis-trifluoromethyl-phenyl)-N-methyl-isobutyramide (0.40 g, 0.636 mmol) in MeOH (12 mL) was added Pd/C (120 mg) and aqueous HCl (0.078 mL, 37% in H2O) and was put under hydrogen pressure at 10 bars. The reaction mixture was stirred at 60° C. for 20 hours before volatiles were removed, pH adjusted to 8 with aqueous NaOH, and the product extracted with EtOAc. The combined organic phases were dried over Na2SO4, and purification by column chromatography (SiO2, EtOAc/Heptane 1/1) yielded 141 mg (41%) of the title compound as a white powder. ES-MS m/e: 539.2 (M+H+).

Workup

customwere removed
extractionthe product extracted with EtOAc
dry with materialThe combined organic phases were dried over Na2SO4, and purification by column chromatography (SiO2, EtOAc/Heptane 1/1)

Sources & evidence

ORD record: ord-b2af43a040294f5ab07a16bd6f6724e1
Source dataset: uspto-grants-2013_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08487102B2

Reaction notes

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