1,4-Dioxane → 6-(6-Methylpyrazin-2-yl)-1-[6-(4-piperidyl)-2-pyridyl]pyrazolo[4,3-c]pyridine

HRID 57876Notes

Reaction equation

HRID 57876 reaction equation
[CH3:1][C:2]1[N: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]([CH: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][CH:3]=1.O1CCOCC1>Cl>[CH3:1][C:2]1[N: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]([CH:23]5[CH2:28][CH2:27][NH:26][CH2:25][CH2:24]5)[N:22]=4)[C:10]=3[CH:9]=2)[CH:5]=[N:4][CH:3]=1

Participants

4

Reactant 2

HCID 312751,4-Dioxane2×HCID 86707071Tert-butyl 4-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidine-1-carboxylate

Product 1

HCID 727154576-(6-Methylpyrazin-2-yl)-1-[6-(4-piperidyl)-2-pyridyl]pyrazolo[4,3-c]pyridineYield 13%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

A mixture of tert-butyl 4-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperidine-1-carboxylate; B; 110 mg; 0.2332 mmol in hydrogen chloride (4 mol/L) in 1,4-dioxane (2.0 ml, 8.0 mmol) and 1,4-dioxane 2.0 mL was stirred at RT 18 h. The reaction was concentrated and submitted for reverse phase HPLC to give 166 (13 mg) in 13% yield. 1H NMR (400 MHz, DMSO) δ 9.80 (s, 1H), 9.46 (s, 1H), 9.34 (s, 1H), 8.71 (s, 1H), 8.63 (s, 1H), 7.99 (t, J=7.9 Hz, 1H), 7.87 (d, J=8.1 Hz, 1H), 7.29 (d, J=7.5 Hz, 1H), 3.15 (d, J=12.0 Hz, 2H), 2.94 (tt, J=11.8, 3.5 Hz, 1H), 2.76-2.67 (m, 2H), 2.66 (s, 3H), 2.01 (d, J=12.1 Hz, 2H), 1.85 (qd, J=12.2, 3.8 Hz, 2H). MS (ESI) m/z: 372.2.

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-70a0ed9eb4684358aa31a67ea6aa2250
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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