Sodium hydride → 7-[(1-Tert-butylpiperidin-4-yl)oxy]-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1h)-one
Reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][C:8](=[O:20])[N:9]2[C:12]2[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=2[Cl:19])=[C:4]([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=2[Cl:27])[N:3]=1.[C:28]([N:32]1[CH2:37][CH2:36][CH:35]([OH:38])[CH2:34][CH2:33]1)([CH3:31])([CH3:30])[CH3:29].[H-].[Na+]>>[C:28]([N:32]1[CH2:37][CH2:36][CH:35]([O:38][C:2]2[CH:11]=[C:10]3[C:5]([CH:6]=[CH:7][C:8](=[O:20])[N:9]3[C:12]3[C:17]([Cl:18])=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:19])=[C:4]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=3[Cl:27])[N:3]=2)[CH2:34][CH2:33]1)([CH3:31])([CH3:29])[CH3:30]Participants
4
Procedure
The title compound was prepared from 40 mg of 7-bromo-5-(2-chlorophenyl)-1-(2,6-dichlorophenyl)-1,6-naphthyridin-2(1H)-one (COMPOUND HHH2), 55 mg of 1-tert-butylpiperidin-4-ol, and 8 mg of NaH by a procedure analogous to that described in COMPOUND HHH6. Mass spectrum (ESI) 556 (M+1). 1H NMR (500 MHz, CDCl3; doubling of peaks due to restricted rotation) δ 1.44 and 1.42 (2 s, 9H); 2.20-2.53 (m, 4H); 2.77 (m, 0.6H); 3.05 (br s, 1.6H); 3.50 (m, 1.5H); 3.70 (m, 0.8H); 4.60-5.40 (m, 2.9H); 5.39 (br s, 0.8H); 5.75 and 5.80 (2 s, 1H); 6.54 and 6.56 (2 d, J=8.5 Hz and J=10 Hz, 1H); 7.36-7.66 (m, 8H).
Sources & evidence
- ORD record
- ord-1397cfe8e57f470c80d53e1a2fc59b54
- Source dataset
- uspto-grants-2004_10
- Patent number
- US06809199B2
Reaction notes
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