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

HRID 57832Notes

Reaction equation

HRID 57832 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[CH2:33][CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1>>[N:27]1([C:2]2[N:7]=[C:6]([N:8]3[C:16]4[CH:15]=[C:14]([C:17]5[CH:18]=[N:19][CH:20]=[C:21]([CH:23]6[CH2:26][O:25][CH2:24]6)[CH:22]=5)[N:13]=[CH:12][C:11]=4[CH:10]=[N:9]3)[CH:5]=[CH:4][CH:3]=2)[CH2:33][CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1

Participants

3

Reactant 2

HCID 68163Hexahydro-1,4-diazepineHCID 867070281-(6-fluoropyridin-2-yl)-6-(5-(oxetan-3-yl)pyridin-3-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 867070381-(6-(1,4-diazepan-1-yl)pyridin-2-yl)-6-(5-(oxetan-3-yl)pyridin-3-yl)-1H-pyrazolo[4,3-c]pyridineYield 18%

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 1,4-diazepane, 118 was obtained as an off-white solid (22.8 mg, 18%). 1H NMR (400 MHz, DMSO) δ 9.36-9.33 (s, 1H), 9.18-9.13 (t, J=4.0 Hz, 1H), 9.10-9.05 (s, 1H), 8.68-8.62 (d, J=5.1 Hz, 2H), 8.55-8.50 (s, 1H), 7.74-7.69 (dd, J=13.8, 5.6 Hz, 1H), 7.23-7.18 (d, J=7.7 Hz, 1H), 6.65-6.61 (d, J=8.5 Hz, 1H), 5.07-5.00 (dd, J=8.3, 6.1 Hz, 2H), 4.76-4.69 (t, J=6.3 Hz, 2H), 4.48-4.36 (m, 1H), 3.90-3.83 (t, J=5.8 Hz, 2H), 3.83-3.77 (d, J=5.3 Hz, 2H), 3.01-2.93 (m, 2H), 2.75-2.69 (m, 2H), 1.89-1.83 (m, 2H); MS (ESI) m/z: 428.2 [M+H]+

Sources & evidence

ORD record
ord-750a8be56ba04f67a23bc9efb101543f
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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