Hydrochloric Acid → 6-(6-methylpyrazin-2-yl)-1-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57835Notes

Reaction equation

HRID 57835 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]([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][CH:3]=1.Cl>O1CCOCC1>[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]([N: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 313Hydrochloric AcidHCID 86707040Tert-butyl 4-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate

Product 1

HCID 727152106-(6-methylpyrazin-2-yl)-1-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridineYield 55%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of tert-butyl 4-[6-[6-(6-methylpyrazin-2-yl)pyrazolo[4,3-c]pyridin-1-yl]-2-pyridyl]piperazine-1-carboxylate (60 mg, 0.1270 mmol) in 1,4-dioxane; 1.0 mL and hydrogen chloride (4 mol/L) in 1,4-dioxane (2.0 mL, 8.0 mmol) was stirred at RT 18 h. The reaction was concentrated and submitted for reverse phase HPLC to give 123 (26 mg) in 32% yield. MS (ESI) m/z: 373.2. 1H NMR (400 MHz, DMSO) δ 9.59 (s, 1H), 9.46 (s, 1H), 9.31 (s, 1H), 8.66 (s, 1H), 8.62 (s, 1H), 7.77 (t, J=8.1 Hz, 1H), 7.27 (d, J=7.7 Hz, 1H), 6.80 (d, J=8.4 Hz, 1H), 3.67-3.60 (m, 4H), 2.96-2.89 (m, 4H), 2.63 (s, 3H).

Workup

  1. concentrationThe reaction was concentrated

Sources & evidence

ORD record
ord-14de3f5ac4dc4ca7b012a0a0ca43e680
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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