Hydrochloric Acid → (S)-1-(3-methoxy-6-(6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-amine

HRID 57896Notes

Reaction equation

HRID 57896 reaction equation
[CH3:1][O:2][C:3]1[C:4]([N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31]C(=O)OC(C)(C)C)[CH2:26]2)=[N:5][C:6]([N:9]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[CH:7][CH:8]=1.Cl>CO.O1CCOCC1>[CH3:1][O:2][C:3]1[C:4]([N:25]2[CH2:30][CH2:29][CH2:28][C@H:27]([NH2:31])[CH2:26]2)=[N:5][C:6]([N:9]2[C:17]3[CH:16]=[C:15]([C:18]4[CH:23]=[N:22][CH:21]=[C:20]([CH3:24])[N:19]=4)[N:14]=[CH:13][C:12]=3[CH:11]=[N:10]2)=[CH:7][CH:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86707087tert-butyl N-[(3S)-1-[3-methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate

Product 1

HCID 77050662(S)-1-(3-methoxy-6-(6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-amineYield 91.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 312751,4-DioxaneSolvent

Procedure

To a solution of tert-butyl N-[(3S)-1-[3-methoxy-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate (0.2758 mmol; 142.5 mg) in Methanol (10 mL) was added hydrochloric acid, 4.0 M in 1,4-Dioxane (5 mL). The resulting mixture was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 186 as an off-white solid (105.6 mg, 91%). 1H NMR (400 MHz, DMSO) δ 9.66-9.62 (s, 1H), 9.48-9.44 (s, 1H), 9.33-9.28 (s, 1H), 8.65-8.61 (d, J=3.5 Hz, 2H), 7.54-7.45 (dd, J=21.6, 8.5 Hz, 2H), 4.02-3.96 (d, J=10.3 Hz, 1H), 3.90-3.84 (d, J=11.7 Hz, 4H), 3.03-2.96 (d, J=9.0 Hz, 1H), 2.89-2.82 (m, 1H), 2.65-2.61 (s, 3H), 1.98-1.86 (t, J=10.6 Hz, 2H), 1.78-1.67 (d, J=10.2 Hz, 1H), 1.45-1.35 (dd, J=19.2, 8.9 Hz, 1H); MS (ESI) m/z: 417.2 [M+H]+

Workup

  1. concentrationThe mixture was concentrated
  2. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-ccf232aea18241d583f93a5a8636811c
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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