Dichloromethane → 1-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-amine

HRID 1774989Notes

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[CH:17]=[C:18]([N:22]5[CH2:27][CH2:26][CH:25]([NH:28]C(=O)OC(C)(C)C)[CH2:24][CH2:23]5)[CH:19]=[N:20][CH:21]=4)=[N:14][N:13](C4CCCCO4)[C:10]3=[CH:11][N:12]=2)[CH:2]=1.C(Cl)Cl.FC(F)(F)C(O)=O>>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:8]=[C:9]3[C:15]([C:16]4[CH:17]=[C:18]([N:22]5[CH2:27][CH2:26][CH:25]([NH2:28])[CH2:24][CH2:23]5)[CH:19]=[N:20][CH:21]=4)=[N:14][NH:13][C:10]3=[CH:11][N:12]=2)[CH:2]=1

Participants

Reactant 3

HCID 6344Dichloromethane

HCID 6422Trifluoroacetic acid

HCID 71253755tert-butyl 1-(5-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate

Product 1

HCID 712538431-(5-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-amineYield 33%

Procedure

To a solution of tert-butyl 1-(5-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-3-yl)piperidin-4-ylcarbamate in methylene chloride (1.00 mL, 15.6 mmol) was added trifluoroacetic Acid (0.3109 mL, 4.036 mmol). The reaction was stirred at RT for 18 hours. The reaction was concentrated then submitted for rHPLC (reverse phase HPLC) to give 158 (10 mg, 33% yield). ESI MS m/z=372.1 (M+1). 1H NMR (400 MHz, DMSO) δ 9.39 (s, 1H), 9.24 (s, 1H), 8.72 (s, 1H), 8.61-8.52 (m, 3H), 8.42 (s, 1H), 7.83 (s, 1H), 7.55-7.48 (m, 1H), 3.85 (d, J=13.0 Hz, 2H), 2.98-2.76 (m, 3H), 1.91-1.81 (m, 2H), 1.42 (dd, J=20.7, 10.2 Hz, 2H)

Workup

concentrationThe reaction was concentrated

Sources & evidence

ORD record: ord-51bd0d02b9434392bf68ddb2f35871fc
Source dataset: uspto-grants-2016_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09260425B2

Reaction notes

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