1-Butanol → 6-butoxy-N-[4-(difluoromethyl)-2-pyridyl]-4-[1-(oxetan-3-yl)-4-piperidyl]pyridin-2-amine
Reaction equation
[CH2:1]([OH:5])[CH2:2][CH2:3][CH3:4].Cl[C:7]1[N:12]=[C:11]([NH:13][C:14]2[CH:19]=[C:18]([CH:20]([F:22])[F:21])[CH:17]=[CH:16][N:15]=2)[CH:10]=[C:9]([CH:23]2[CH2:28][CH2:27][N:26]([CH:29]3[CH2:32][O:31][CH2:30]3)[CH2:25][CH2:24]2)[CH:8]=1>>[CH2:1]([O:5][C:7]1[N:12]=[C:11]([NH:13][C:14]2[CH:19]=[C:18]([CH:20]([F:22])[F:21])[CH:17]=[CH:16][N:15]=2)[CH:10]=[C:9]([CH:23]2[CH2:28][CH2:27][N:26]([CH:29]3[CH2:30][O:31][CH2:32]3)[CH2:25][CH2:24]2)[CH:8]=1)[CH2:2][CH2:3][CH3:4]Participants
3
Procedure
Reaction of n-butanol (3 equiv) with 6-chloro-N-(4-(difluoromethyl)pyridin-2-yl)-4-(1-(oxetan-3-yl)piperidin-4-yl)pyridin-2-amine (50.0 mg, 0.127 mmol) following general Beller etherification procedure afforded the target compound as a colorless solid (17.0 mg, 31%); 1H NMR (400 MHz, DMSO) δ 9.77 (s, 1H), 8.35 (d, J=5.1 Hz, 1H), 8.22 (s, 1H), 7.19-6.86 (m, 3H), 6.18 (s, 1H), 4.57-4.51 (m, 2H), 4.48-4.42 (m, 2H), 4.25 (t, J=6.8 Hz, 2H), 3.45-3.36 (m, 1H), 2.83-2.75 (m, 2H), 2.46-2.37 (m, 1H), 1.90-1.79 (m, 2H), 1.78-1.55 (m, 6H), 1.49-1.38 (m, 2H), 0.93 (t, J=7.4 Hz, 3H); ESI-LRMS m/z [M+1]+=433.
Sources & evidence
- ORD record
- ord-5e4c6c604e3c47c083430ea1ebde58f5
- Source dataset
- uspto-grants-2016_07
- Patent number
- US09399636B2
Reaction notes
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