Potassium Carbonate → (+/-)-5-[(1-{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl)oxy]-2-[4-(methylsulfonyl)phenyl]pyridine

HRID 423612Notes

Reaction equation

HRID 423612 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].CS(O[CH:23]([CH:25]1[CH2:30][CH2:29][N:28]([C:31]2[O:35][N:34]=[C:33]([CH:36]([CH3:38])[CH3:37])[N:32]=2)[CH2:27][CH2:26]1)[CH3:24])(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:38][CH:36]([C:33]1[N:32]=[C:31]([N:28]2[CH2:27][CH2:26][CH:25]([CH:23]([O:17][C:14]3[CH:13]=[CH:12][C:11]([C:8]4[CH:7]=[CH:6][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:10][CH:9]=4)=[N:16][CH:15]=3)[CH3:24])[CH2:30][CH2:29]2)[O:35][N:34]=1)[CH3:37]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 532295926-(4-(Methylsulfonyl)phenyl)pyridin-3-olHCID 86638745HCID 86638745, compound

Product 1

HCID 59177801(+/-)-5-[(1-{1-[3-(1-Methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl)oxy]-2-[4-(methylsulfonyl)phenyl]pyridine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound (0.295 g, 54%) was prepared as a white foam from 6-[4-(methylsulfonyl)phenyl]-3-pyridinol (0.29 g, 1.16 mmol), (±)-1-{1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}ethyl methanesulfonate (0.53 g, crude), K2CO3 (0.32 g, 2.32 mmol) in DMF (10 mL) in a manner similar to Example 139, Step 3. The crude material was purified by chromatography on a silica gel column eluted with 1:7 acetone/CH2Cl2 to give the title compound as a white foam. 1H NMR (400 MHz, CDCl3): δ 8.38 (d, 1H, J=3.0 Hz), 8.13 (d, 2H, J=8.5 Hz), 8.00 (d, 2H, J=8.6 Hz), 7.74 (d, 1H, J=8.8 Hz), 7.35-7.25 (m, 1H), 4.35-4.25 (m, 1H), 4.25-4.15 (m, 2H), 3.10-3.00 (m, 5H), 2.87 (septet, 1H, J=7.0 Hz), 2.05-1.95 (m, 1H), 1.95-1.75 (m, 2H), 1.40-1.20 (m, 2H), 1.34 (d, 3H, J=6.3 Hz), 1.27 (d, 6H, J=6.9 Hz); LRMS (ESI), m/z 471 (M+H).

Workup

  1. customThe crude material was purified by chromatography on a silica gel column
  2. washeluted with 1:7 acetone/CH2Cl2

Sources & evidence

ORD record
ord-d403cd7a16154cbe82946990922eec0e
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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