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

HRID 57820Notes

Reaction equation

HRID 57820 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[CH2:32][CH2:31]C[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[CH2:27][CH2:28][NH:29][CH2:31][CH2:32]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 68163Hexahydro-1,4-diazepineHCID 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 22%

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 1,4-diazepane, 112 was obtained as an off-white solid (30.9 mg, 22%). 1H NMR (400 MHz, DMSO) δ 9.37-9.25 (s, 1H), 9.04-8.98 (s, 2H), 8.67-8.59 (s, 1H), 8.51-8.45 (d, J=2.1 Hz, 1H), 8.05-7.99 (t, J=2.1 Hz, 1H), 7.74-7.66 (dd, J=14.5, 6.5 Hz, 1H), 7.24-7.15 (t, J=7.4 Hz, 1H), 6.65-6.58 (d, J=8.5 Hz, 1H), 3.90-3.73 (dt, J=10.0, 5.5 Hz, 4H), 3.00-2.91 (m, 2H), 2.75-2.65 (dd, J=13.3, 7.3 Hz, 2H), 2.12-2.04 (m, 1H), 1.91-1.81 (m, 2H), 1.12-1.03 (m, 2H), 0.88-0.81 (m, 2H).; MS (ESI) m/z: 412.2 [M+H]+

Sources & evidence

ORD record
ord-66c725923aab43ffa87ebbe3371f45f9
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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