(3R)-piperidin-3-ol hydrochloride → HCID 71254070, compound

HRID 1775092Notes

Reaction equation

HRID 1775092 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[N:11](COCC[Si](C)(C)C)[N:10]=2)=[N:6][C:7]=1F.Cl.[NH:33]1[CH2:38][CH2:37][CH2:36][C@@H:35]([OH:39])[CH2:34]1>>[Br:1][C:2]1[C:7]([N:33]2[CH2:38][CH2:37][CH2:36][C@@H:35]([OH:39])[CH2:34]2)=[N:6][C:5]([C:9]2[C:17]3[C:12](=[CH:13][N:14]=[C:15]([C:18]4[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=4)[CH:16]=3)[NH:11][N:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 2759333(3R)-piperidin-3-ol hydrochlorideHCID 71253450HCID 71253450, compound

Product 1

HCID 71254070HCID 71254070, compoundYield 29.9%

Procedure

Following the procedures as described in Example 241 and starting with 3-(5-bromo-6-fluoropyridin-2-yl)-5-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrazolo[3,4-c]pyridine and (R)-piperidin-3-ol hydrochloride, 291 was obtained as an off-white solid (11.0 mg, 29.9%) over two steps. 1H NMR (400 MHz, DMSO) δ 9.31 (d, J=1.8 Hz, 1H), 9.24 (s, 1H), 9.01 (s, 1H), 8.60 (d, J=4.0 Hz, 1H), 8.44 (d, J=8.1 Hz, 1H), 8.06 (d, J=8.1 Hz, 1H), 7.70 (d, J=8.1 Hz, 1H), 7.51 (dd, J=8.0, 4.8 Hz, 1H), 4.93 (d, J=4.4 Hz, 1H), 3.97 (d, J=11.6 Hz, 1H), 3.83 (d, J=12.2 Hz, 1H), 3.74 (dd, J=9.2, 4.8 Hz, 1H), 2.99-2.81 (m, 2H), 2.02 (d, J=9.1 Hz, 1H), 1.88 (d, J=13.3 Hz, 1H), 1.72 (dd, J=22.7, 10.5 Hz, 1H), 1.39 (dd, J=22.0, 8.0 Hz, 1H); ESI MS m/z=451.1 (M+1)

Sources & evidence

ORD record
ord-60b4ec087f0e408bb51d8d9d54c10fb7
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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