tert-butyl N-[(3S)-1-[6-[6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate → (3S)-1-[6-[6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidin-3-amine

HRID 57816Notes

Reaction equation

HRID 57816 reaction equation
[CH:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:15]=[CH:14][C:13]3[CH:16]=[N:17][N:18]([C:19]4[N:24]=[C:23]([N:25]5[CH2:30][CH2:29][CH2:28][C@H:27]([NH:31]C(=O)OC(C)(C)C)[CH2:26]5)[CH:22]=[CH:21][CH:20]=4)[C:12]=3[CH:11]=2)[CH:7]=[N:8][CH:9]=1)([CH3:3])[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH:1]([C:4]1[CH:5]=[C:6]([C:10]2[N:15]=[CH:14][C:13]3[CH:16]=[N:17][N:18]([C:19]4[N:24]=[C:23]([N:25]5[CH2:30][CH2:29][CH2:28][C@H:27]([NH2:31])[CH2:26]5)[CH:22]=[CH:21][CH:20]=4)[C:12]=3[CH:11]=2)[CH:7]=[N:8][CH:9]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 86707023tert-butyl N-[(3S)-1-[6-[6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate

Product 1

HCID 86707024(3S)-1-[6-[6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidin-3-amineYield 37%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

The aforesaid tert-butyl N-[(3S)-1-[6-[6-(5-isopropyl-3-pyridyl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]-3-piperidyl]carbamate in DCM (5 mL) and TFA (5 mL) was stirred at room temperature for 1 h. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 108 (33.9 mg, 37%). 1H NMR (400 MHz, DMSO) δ 9.35-9.30 (s, 1H), 9.13-9.10 (d, J=2.0 Hz, 1H), 9.06-9.02 (s, 1H), 8.66-8.61 (s, 1H), 8.58-8.55 (d, J=2.0 Hz, 1H), 8.35-8.31 (d, J=1.9 Hz, 1H), 7.78-7.70 (t, J=8.1 Hz, 1H), 7.23-7.17 (d, J=7.7 Hz, 1H), 6.84-6.78 (d, J=8.5 Hz, 1H), 4.32-4.14 (dd, J=37.4, 11.8 Hz, 2H), 3.12-3.01 (td, J=12.8, 5.7 Hz, 2H), 2.87-2.70 (ddd, J=15.5, 13.1, 7.6 Hz, 2H), 1.96-1.74 (m, 2H), 1.64-1.51 (dd, J=24.5, 11.5 Hz, 2H), 1.33-1.31 (d, J=7.0 Hz, 6H); MS (ESI) m/z: 414.1 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-44b1168683974fd5acbfefd86b40e27b
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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