Hydrochloric Acid → HCID 71254149, compound

HRID 1775078Notes

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][CH:25]([CH2:28][NH:29]C(=O)OC(C)(C)C)[CH2:24][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][CH:25]([CH2:28][NH2:29])[CH2:24][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: 70 °C

Procedure

To a solution of tert-butyl (1-(6-(5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-yl)methylcarbamate (190 mg, 0.31 mmol) in dioxane (5 mL), was added 10% HCl (1 mL). The reaction mixture was heated at 70° C. for 2 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 278 as a yellow solid (60 mg, 50%). 1H NMR (400 MHz, DMSO) 9.23 (s, 2H), 8.95 (s, 1H), 8.61-8.60 (d, J=2.8, 1H), 8.40-8.38 (m, 1H), 7.68-7.65 (m, 1H), 7.58-7.55 (m, 1H), 7.48-7.46 (m, 1H), 4.96 (s, 1H), 4.53-4.50 (d, J=10.4, 1H), 3.38-3.36 (m, 3H), 2.69-2.68 (d, J=4, 2H), 188-1.86 (d, J=8.3H), 1.32-1.30 (m, 3H). ESI MS m/z=385.2 (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-0d86bed8bb984c74bc1ca8a9ae6b0b34
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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