Hydrochloric Acid → HCID 22347066, compound

HRID 432243Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:29]3[CH2:34][CH2:33][N:32](C(OC(C)(C)C)=O)[CH2:31][CH2:30]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:22]=[C:23]([CH3:27])[CH:24]=[CH:25][CH:26]=4)=[O:19])=[C:13]([F:28])[CH:12]=3)[C:3]=12.[ClH:42].[Cl:43]CCl>CC(C)=O>[ClH:43].[ClH:42].[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([CH:29]3[CH2:34][CH2:33][NH:32][CH2:31][CH2:30]3)[N:9]=[C:10]([C:11]3[CH:16]=[CH:15][C:14]([NH:17][C:18]([NH:20][C:21]4[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=4)=[O:19])=[C:13]([F:28])[CH:12]=3)[C:3]=12

Participants

Conditions

Temperature: 0 °C

Procedure

tert-Butyl 4-(4-amino-3-{3-fluoro-4-[(3-toluidinocarbonyl)amino]phenyl}-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-1-piperidinecarboxylate (117 mg, 0.209 mmol) was suspended in acetone (7 mL) and cooled to 0° C. Aqueous hydrochloric acid (6N, 1.6 mL) was slowly added to the reaction mixture. The reaction mixture was warmed to room temperature then heated at 50° C. for 4 hours. Concentration of the reaction mixture under reduced pressure followed by trituration with dichloromethane (25 mL) afforded N-{4-[4-amino-1-(4-piperidyl)-1H-pyrazolo[3,4-d]pyrimidin-3-yl]-2-fluorophenyl}-N′-(3-methylphenyl)urea dihydrochloride salt as an off-white solid (111 mg, 0.241 mmol). HPLC-RT: 11.98 min. (flow rate: 1 mL/min λ=254 nm Gradient: 5% to 85% acetonitrile/0.1M aqueous ammonium acetate gradient over 20 min.; Deltapak C18, 300A, 5 μm, 150×3.9 mm column); m/z (MH+)=461.3.

Workup

temperatureThe reaction mixture was warmed to room temperature
temperaturethen heated at 50° C. for 4 hours

Sources & evidence

ORD record: ord-8bc2d358363644198246c15f25c2e18e
Source dataset: uspto-grants-2003_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06660744B1

Reaction notes

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