Piperazine → 6-(5-ethylpyridin-3-yl)-1-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine

HRID 57810Notes

Reaction equation

HRID 57810 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20](F)[N:19]=4)[C:11]=3[CH:10]=2)[CH:6]=[N:7][CH:8]=1)[CH3:2].[NH:25]1[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]1>>[CH2:1]([C:3]1[CH:4]=[C:5]([C:9]2[N:14]=[CH:13][C:12]3[CH:15]=[N:16][N:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([N:25]5[CH2:30][CH2:29][NH:28][CH2:27][CH2:26]5)[N:19]=4)[C:11]=3[CH:10]=2)[CH:6]=[N:7][CH:8]=1)[CH3:2]

Participants

3

Reactant 2

HCID 4837PiperazineHCID 867070186-(5-ethylpyridin-3-yl)-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 867070176-(5-ethylpyridin-3-yl)-1-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridineYield 18%

Procedure

Following the procedures as described in EXAMPLE 8 and starting with 6-(5-ethylpyridin-3-yl)-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine and piperazine, 104 was obtained as an off-white solid (22.3 mg, 18%) over 2 steps. 1H NMR (400 MHz, DMSO) δ 9.35-9.27 (s, 1H), 9.16-9.08 (d, J=2.0 Hz, 1H), 9.08-9.01 (s, 1H), 8.67-8.59 (s, 1H), 8.57-8.50 (d, J=1.9 Hz, 1H), 8.30-8.21 (s, 1H), 7.85-7.73 (m, 2H), 7.66-7.44 (m, 2H), 7.28-7.23 (d, J=7.7 Hz, 1H), 6.85-6.78 (d, J=8.4 Hz, 1H), 3.65-3.57 (m, 4H), 2.98-2.81 (m, 4H), 2.79-2.70 (q, J=7.6 Hz, 2H), 1.75-1.52 (m, 3H), 1.32-1.24 (t, J=7.6 Hz, 3H).; MS (ESI) m/z: 386.2 [M+H]+

Sources & evidence

ORD record
ord-ab3947ade8a6486186de3f724ecf2efd
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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