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

HRID 1775045Notes

Reaction equation

HRID 1775045 reaction equation
[C:1]([C:4]1([NH:37]C(=O)OC(C)(C)C)[CH2:9][CH2:8][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[C:24]4[C:19](=[CH:20][N:21]=[C:22]([C:25]5[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=5)[CH:23]=4)[N:18](C4CCCCO4)[N:17]=3)[N:11]=2)[CH2:6][CH2:5]1)(=[O:3])[NH2:2].Cl>CO.O1CCOCC1>[NH2:37][C:4]1([C:1]([NH2:2])=[O:3])[CH2:5][CH2:6][N:7]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]3[C:24]4[C:19](=[CH:20][N:21]=[C:22]([C:25]5[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=5)[CH:23]=4)[NH:18][N:17]=3)[N:11]=2)[CH2:8][CH2:9]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 71253281tert-Butyl 4-carbamoyl-1-(6-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ylcarbamate

Product 1

HCID 712537604-amino-1-(6-(5-(pyridin-3-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidine-4-carboxamideYield 60.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 45 mg (0.08 mmol) of tert-butyl 4-carbamoyl-1-(6-(5-(pyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridin-3-yl)pyridin-2-yl)piperidin-4-ylcarbamate in 3 ml of methanol and 12 ml of 4 N solution of HCl in dioxane was stirred for 18 hours. The mixture was concentrated in vacuum, the residue purified via reverse phase HPLC using a gradient of MeCN in water with 0.1% HCOOH to afford 20 mg (43%) of 229. ESI MS m/z 415.2 (M+1). 1H NMR (400 MHz, DMSO): 9.22 (d, J=5.7 Hz, 2H), 8.94 (s, 1H), 8.60 (d, J=4.6 Hz, 1H), 8.40-8.32 (m, 4H), 7.67 (t, J=7.9 Hz, 1H), 7.54 (dd, J=8.0, 4.8 Hz, 1H), 7.46 (d, J=7.4 Hz, 1H), 6.95 (s, 1H), 6.90 (d, J=8.5 Hz, 1H), 4.20 (d, J=13.2 Hz, 1H), 3.50 (t, J=11.4 Hz, 1H), 2.06 (td, J=13.0, 4.2 Hz, 1H), 1.48 (d, J=13.2 Hz, 1H).

Workup

  1. concentrationThe mixture was concentrated in vacuum
  2. customthe residue purified via reverse phase HPLC

Sources & evidence

ORD record
ord-5e334baf98814bab86fffe67d1eb0653
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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