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

HRID 57824Notes

Reaction equation

HRID 57824 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][CH:32]([OH:34])[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[N:7]=[C:2]([N:27]6[CH2:33][CH:32]([OH:34])[CH2:31][NH:30][CH2:29][CH2:28]6)[CH:3]=[CH:4][CH:5]=5)[C:16]=4[CH:15]=3)[CH:18]=[N:19][CH:20]=2)[CH2:24]1

Participants

3

Reactant 2

HCID 211142751,4-Diazepan-6-olHCID 867070281-(6-fluoropyridin-2-yl)-6-(5-(oxetan-3-yl)pyridin-3-yl)-1H-pyrazolo[4,3-c]pyridine

Product 1

HCID 727151371-(6-(6-(5-(oxetan-3-yl)pyridin-3-yl)-1H-pyrazolo[4,3-c]pyridin-1-yl)pyridin-2-yl)-1,4-diazepan-6-olYield 6%

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-diazepan-6-ol, 116 was obtained as an off-white solid (7.2 mg, 6%). 1H NMR (400 MHz, DMSO) δ 9.35-9.29 (s, 1H), 9.23-9.16 (dd, J=8.9, 2.0 Hz, 1H), 9.11-9.04 (d, J=8.6 Hz, 1H), 8.77-8.62 (m, 2H), 8.55-8.46 (dd, J=15.4, 8.6 Hz, 1H), 7.74-7.67 (t, J=8.1 Hz, 1H), 7.21-7.16 (d, J=7.7 Hz, 1H), 6.77-6.68 (dd, J=8.5, 2.9 Hz, 1H), 5.69-5.45 (d, J=72.4 Hz, 1H), 5.06-5.00 (dd, J=8.1, 6.2 Hz, 1H), 4.81-4.70 (dd, J=13.5, 6.7 Hz, 2H), 4.48-4.40 (m, 1H), 4.06-3.85 (dd, J=32.4, 13.9 Hz, 3H), 3.74-3.53 (m, 2H), 3.00-2.93 (d, J=2.3 Hz, 2H), 2.83-2.77 (dd, J=13.8, 3.8 Hz, 1H), 2.70-2.62 (dd, J=13.2, 6.0 Hz, 1H); MS (ESI) m/z: 444.2 [M+H]+

Sources & evidence

ORD record
ord-e63e13aef72047c49702b4240684b267
Source dataset
uspto-grants-2016_09
Patent number
US09434725B2

Reaction notes

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