3-Hydroxypiperidine → HCID 71253412, compound

HRID 1775068Notes

Reaction equation

HRID 1775068 reaction equation
F[C:2]1[N:7]=[C:6]([C:8]2[C:16]3[C:11](=[CH:12][N:13]=[C:14]([C:17]4[CH:18]=[N:19][N:20]([CH3:22])[CH:21]=4)[CH:15]=3)[N:10](C3CCCCO3)[N:9]=2)[CH:5]=[CH:4][CH:3]=1.[NH:29]1[CH2:34][CH2:33][CH2:32][CH:31]([OH:35])[CH2:30]1>>[CH3:22][N:20]1[CH:21]=[C:17]([C:14]2[CH:15]=[C:16]3[C:8]([C:6]4[N:7]=[C:2]([N:29]5[CH2:34][CH2:33][CH2:32][CH:31]([OH:35])[CH2:30]5)[CH:3]=[CH:4][CH:5]=4)=[N:9][NH:10][C:11]3=[CH:12][N:13]=2)[CH:18]=[N:19]1

Participants

3

Reactant 2

HCID 232933-HydroxypiperidineHCID 712534393-(6-fluoropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine

Product 1

HCID 71253412HCID 71253412, compoundYield 62.8%

Procedure

Following the procedures as described in Example 189, 3-(6-fluoropyridin-2-yl)-5-(1-methyl-1H-pyrazol-4-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-c]pyridine and piperidin-3-ol were reacted. The product was deprotected and purified to give 262 as a white solid (62.8% over two steps). 1H NMR δ 13.68 (broad s, 1H), 9.03 (s, 1H), 8.60 (s, 1H), 8.24 (s, 1H), 7.96 (s, 1H), 7.67-7.58 (m, 1H), 7.42 (d, J=7.4 Hz, 1H), 6.83 (d, J=8.5 Hz, 1H), 5.04 (d, J=5.1 Hz, 1H), 4.59-4.49 (m, 1H), 4.08 (d, J=13.1 Hz, 1H), 3.89 (s, 3H), 3.65 (dt, J=14.0, 4.8 Hz, 1H), 3.05 (dd, J=17.1, 6.8 Hz, 1H), 2.91 (dd, J=12.4, 9.4 Hz, 1H), 2.07-1.97 (m, 1H), 1.91-1.78 (m, 1H), 1.65-1.42 (m, 2H). LC/MS: m/z 376.1 [M+1]

Workup

  1. customwere reacted
  2. custompurified

Sources & evidence

ORD record
ord-977f0c7ed09c4330a03c7b07987b7138
Source dataset
uspto-grants-2016_02
Patent number
US09260425B2

Reaction notes

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