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

HRID 57822Notes

Reaction equation

HRID 57822 reaction equation
F[C:2]1[N:7]=[C:6]([N:8]2[C:16]3[CH:15]=[C:14]([C:17]4[CH:18]=[N:19][CH:20]=[C:21]([CH:23]5[CH2:26][O:25][CH2:24]5)[CH:22]=4)[N:13]=[CH:12][C:11]=3[CH:10]=[N:9]2)[CH:5]=[CH:4][CH:3]=1.[NH:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[O:25]1[CH2:26][CH:23]([C:21]2[CH:22]=[C:17]([C:14]3[N:13]=[CH:12][C:11]4[CH:10]=[N:9][N:8]([C:6]5[CH:5]=[CH:4][CH:3]=[C:2]([N:27]6[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]6)[N:7]=5)[C:16]=4[CH:15]=3)[CH:18]=[N:19][CH:20]=2)[CH2:24]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 867070281-(6-fluoropyridin-2-yl)-6-(5-(oxetan-3-yl)pyridin-3-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 867070296-(5-(oxetan-3-yl)pyridin-3-yl)-1-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridineYield 13%

Procedure

Following the procedures as described in EXAMPLE 8 and starting with 1-(6-fluoropyridin-2-yl)-6-(5-(oxetan-3-yl)pyridin-3-yl)-1H-pyrazolo[4,3-c]pyridine and piperazine, 114 was obtained as an off-white solid (14.3 mg, 13%). 1H NMR (400 MHz, DMSO) δ 9.36-9.31 (s, 1H), 9.20-9.14 (d, J=2.1 Hz, 1H), 9.10-9.05 (s, 1H), 8.70-8.62 (m, 2H), 8.57-8.52 (t, J=2.0 Hz, 1H), 7.81-7.74 (t, J=8.1 Hz, 1H), 7.28-7.22 (d, J=7.7 Hz, 1H), 6.85-6.78 (d, J=8.4 Hz, 1H), 5.08-5.00 (dd, J=8.3, 6.1 Hz, 2H), 4.77-4.70 (t, J=6.3 Hz, 2H), 4.47-4.38 (m, 1H), 3.65-3.56 (m, 4H), 2.99-2.75 (m, 4H).; MS (ESI) m/z: 414.2 [M+H]+

Sources & evidence

ORD record
ord-8d257f50c5c748038868ef72212aeb78
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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