tert-butyl N-[(3S)-1-[3-fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate → (S)-1-(3-fluoro-6-(6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-amine

HRID 57916Notes

Reaction equation

HRID 57916 reaction equation
[F:1][C:2]1[C:3]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH:30]C(=O)OC(C)(C)C)[CH2:25]2)=[N:4][C:5]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1>C(O)(C(F)(F)F)=O.ClCCl>[F:1][C:2]1[C:3]([N:24]2[CH2:29][CH2:28][CH2:27][C@H:26]([NH2:30])[CH2:25]2)=[N:4][C:5]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:22]=[N:21][CH:20]=[C:19]([CH3:23])[N:18]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 86707107tert-butyl N-[(3S)-1-[3-fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate

Product 1

HCID 72714386(S)-1-(3-fluoro-6-(6-(6-methylpyrazin-2-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperidin-3-amineYield 78.5%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl N-[(3S)-1-[3-fluoro-6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate (0.1345 mmol; 113.1 mg) in TFA (1 mL) and dichloromethane (4 mL) was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 215 as an off-white solid (42.7 mg, 77%). 1H NMR (400 MHz, DMSO) δ 9.58-9.55 (s, 1H), 9.47-9.43 (s, 1H), 9.33-9.30 (s, 1H), 8.69-8.65 (s, 1H), 8.64-8.62 (s, 1H), 8.35-8.30 (s, 1H), 7.79-7.72 (dd, J=12.7, 8.5 Hz, 1H), 7.42-7.38 (dd, J=8.4, 2.0 Hz, 1H), 4.05-3.97 (d, J=8.5 Hz, 2H), 3.29-3.26 (d, J=10.8 Hz, 1H), 3.02-2.95 (m, 2H), 2.66-2.60 (s, 3H), 2.00-1.87 (t, J=14.1 Hz, 2H), 1.80-1.67 (m, 1H), 1.47-1.37 (d, J=10.5 Hz, 1H); MS (ESI) m/z: 405.1 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-548cc4c00bf946a088288af0d73b3b6a
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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