Hydrochloric Acid → 4-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-one

HRID 1775080Notes

Reaction equation

[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[N:21]=[C:20]([N:22]5[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]5)[CH:19]=[CH:18][CH:17]=4)=[N:14][N:13](COCC[Si](C)(C)C)[C:10]3=[CH:11][N:12]=2)[CH:2]=1.Cl>O1CCOCC1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[N:21]=[C:20]([N:22]5[CH2:27][CH2:26][NH:25][C:24](=[O:28])[CH2:23]5)[CH:19]=[CH:18][CH:17]=4)=[N:14][NH:13][C:10]3=[CH:11][N:12]=2)[CH:2]=1

Participants

Conditions

Temperature: 25 °C

Procedure

To a solution of 4-(6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperazin-2-one (70 mg, 0.14 mmol) in dioxane (5 mL), was added 10% HCl 1 mL. The reaction mixture was stirred at 25° C. for 16 h, and the reaction was monitored by LCMS. Upon completion of the reaction, the solvent was distilled off and the crude material was purified via reverse phase prep-HPLC eluting with 40% to 80% MeOH in aqueous 0.1% NH4OH solution to afford 279 as a yellow solid (13 mg, 25%). 1H NMR (400 MHz, DMSO) δ 9.28 (s, 1H), 9.13 (s, 1H), 9.02 (s, 1H), 8.58-8.53 (m, 2H), 7.76-7.73 (t, 1H), 7.64-7.60 (m, 2H), 6.88-6.87 (d, J=6.4, 1H), 4.39 (s, 2H), 3.99-3.98 (t, J=4, 2H). ESI MS m/z=371.15 (M+1)

Workup

customUpon completion of the reaction
distillationthe solvent was distilled off
customthe crude material was purified via reverse phase
washprep-HPLC eluting with 40% to 80% MeOH in aqueous 0.1% NH4OH solution

Sources & evidence

ORD record: ord-50f2ca7b708d4eab84f097a4346da45d
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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