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

HRID 57819Notes

Reaction equation

HRID 57819 reaction equation
[CH:1]1([C:4]2[CH:5]=[C:6]([C:10]3[N:15]=[CH:14][C:13]4[CH:16]=[N:17][N:18]([C:19]5[CH:24]=[CH:23][CH:22]=[C:21](F)[N:20]=5)[C:12]=4[CH:11]=3)[CH:7]=[N:8][CH:9]=2)[CH2:3][CH2:2]1.[NH:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1>>[CH:1]1([C:4]2[CH:5]=[C:6]([C:10]3[N:15]=[CH:14][C:13]4[CH:16]=[N:17][N:18]([C:19]5[CH:24]=[CH:23][CH:22]=[C:21]([N:26]6[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]6)[N:20]=5)[C:12]=4[CH:11]=3)[CH:7]=[N:8][CH:9]=2)[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 4837PiperazineHCID 867070276-(5-cyclopropylpyridin-3-yl)-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 727151346-(5-cyclopropylpyridin-3-yl)-1-(6-(piperazin-1-yl)pyridin-2-yl)-1H-pyrazolo[4,3-c]pyridineYield 31%

Procedure

Following the procedures as described in EXAMPLE 8 and starting with 6-(5-cyclopropylpyridin-3-yl)-1-(6-fluoropyridin-2-yl)-1H-pyrazolo[4,3-c]pyridine and piperazine, 111 was obtained as an off-white solid (41.7 mg, 31%). 1H NMR (400 MHz, DMSO) δ 9.33-9.28 (s, 1H), 9.06-8.99 (d, J=2.5 Hz, 2H), 8.66-8.61 (s, 1H), 8.50-8.45 (d, J=2.1 Hz, 1H), 8.09-8.03 (t, J=2.0 Hz, 1H), 7.81-7.73 (t, J=8.1 Hz, 1H), 7.29-7.20 (d, J=7.7 Hz, 1H), 6.85-6.76 (d, J=8.5 Hz, 1H), 3.65-3.56 (m, 4H), 2.94-2.84 (m, 4H), 2.13-2.04 (m, 1H), 1.12-1.04 (m, 2H), 0.88-0.81 (m, 2H); MS (ESI) m/z: 398.2 [M+H]+

Sources & evidence

ORD record
ord-620834d6204848c092152f03d5366322
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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