tert-butyl 4-(6-(6-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate → 6-(1-Ethylpyrazol-4-yl)-1-(6-piperazin-1-yl-2-pyridyl)pyrazolo[4,3-c]pyridine

HRID 57809Notes

Reaction equation

HRID 57809 reaction equation
[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][N:16]([C:17]4[N:22]=[C:21]([N:23]5[CH2:28][CH2:27][N:26](C(OC(C)(C)C)=O)[CH2:25][CH2:24]5)[CH:20]=[CH:19][CH:18]=4)[C:10]=3[CH:9]=2)[CH:5]=[N:4]1)[CH3:2]>C(Cl)Cl.C(O)(C(F)(F)F)=O>[CH2:1]([N:3]1[CH:7]=[C:6]([C:8]2[N:13]=[CH:12][C:11]3[CH:14]=[N:15][N:16]([C:17]4[CH:18]=[CH:19][CH:20]=[C:21]([N:23]5[CH2:24][CH2:25][NH:26][CH2:27][CH2:28]5)[N:22]=4)[C:10]=3[CH:9]=2)[CH:5]=[N:4]1)[CH3:2]

Participants

4

Reactant 1

HCID 86707016tert-butyl 4-(6-(6-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate

Product 1

HCID 727150446-(1-Ethylpyrazol-4-yl)-1-(6-piperazin-1-yl-2-pyridyl)pyrazolo[4,3-c]pyridineYield 51%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of tert-butyl 4-(6-(6-(1-ethyl-1H-pyrazol-4-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)piperazine-1-carboxylate (0.2486 mmol; 118 mg) in DCM (5 mL) and TFA (5 mL) was stirred at room temperature overnight. The mixture was concentrated and the residue was purified by reverse phase HPLC to afford 6-(1-ethyl-1H-pyrazol-4-yl)-1-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine 101 (47.5 mg, 50%). 1H NMR (400 MHz, DMSO) δ 9.15-9.11 (s, 1H), 8.67-8.65 (s, 1H), 8.54-8.51 (s, 1H), 8.27-8.24 (s, 1H), 7.91-7.88 (s, 1H), 7.78-7.72 (t, J=8.1 Hz, 1H), 7.24-7.18 (d, J=7.7 Hz, 1H), 6.80-6.74 (d, J=8.4 Hz, 1H), 4.26-4.17 (q, J=7.3 Hz, 2H), 3.65-3.56 (m, 4H), 2.96-2.86 (m, 4H), 1.46-1.41 (t, J=7.3 Hz, 3H); MS (ESI) m/z: 375.1 [M+H]+

Workup

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

Sources & evidence

ORD record
ord-9cc97601d11b4ba990a30ea022b74c10
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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