Tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate → Isopropyl 4-((1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)methyl)piperidine-1-carboxylate
Reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:24][CH2:23][N:22]([C:25]([O:27][C:28](C)([CH3:30])[CH3:29])=[O:26])[CH2:21][CH2:20]3)=[CH:13][C:12]2=[O:32])=[CH:7][CH:6]=1)(=[O:4])=[O:3].CS(C1C=CC(N2C=CC(OC3CCN(C(OC(C)(C)C)=O)CC3)=CC2=O)=CC=1)(=O)=O>>[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH:16]=[CH:15][C:14]([O:17][CH2:18][CH:19]3[CH2:20][CH2:21][N:22]([C:25]([O:27][CH:28]([CH3:29])[CH3:30])=[O:26])[CH2:23][CH2:24]3)=[CH:13][C:12]2=[O:32])=[CH:7][CH:6]=1)(=[O:3])=[O:4]Participants
3
Reactant 2
Product 1
Procedure
Example 5 was prepared according to procedures described in Example 3 substituting tert-butyl 4-((1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)methyl)piperidine-1-carboxylate for tert-butyl 4-(1-(4-(methylsulfonyl)phenyl)-2-oxo-1,2-dihydropyridin-4-yloxy)piperidine-1-carboxylate. 1H NMR (500 MHz, CDCl3) δ 8.07 (d, J=8.25 Hz, 2 H), 7.61 (d, J=8.80 Hz, 2 H), 7.23 (d, J=7.70 Hz, 1 H), 6.09 (dd, J=7.70, 2.75 Hz, 1 H), 6.01 (d, J=2.75 Hz, 1 H), 4.87-4.98 (m, 1 H), 4.23 (app brs, 2 H), 3.85 (d, J=6.05 Hz, 2 H), 3.09 (s, 3H), 2.79 (t, J=12.65 Hz, 2 H), 1.87-2.06 (m, 1 H), 1.76-1.87 (d, J=12.10 Hz, 2 H), 1.18-1.37 (m, 6 H), 1.25 (d, J=6.05 Hz, 6 H). MS (ESI) 449 (M+H).
Workup
- customExample 5 was prepared
Sources & evidence
- ORD record
- ord-65852c6f90344187b519d47546fd7ff6
- Source dataset
- uspto-grants-2012_07
- Patent number
- US08232404B2
Reaction notes
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