Potassium Carbonate → HCID 24995589, compound

HRID 423644Notes

Reaction equation

HRID 423644 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:10])=[O:9])[CH:5]=[CH:4][C:3]=1[C:12]1[N:13]=[CH:14][C:15]([OH:18])=[N:16][CH:17]=1.CS(O[CH2:24][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)(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[F:1][C:2]1[CH:7]=[C:6]([S:8]([CH3:11])(=[O:9])=[O:10])[CH:5]=[CH:4][C:3]=1[C:12]1[CH:17]=[N:16][C:15]([O:18][CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]3[O:35][N:34]=[C:33]([CH:36]([CH3:38])[CH3:37])[N:32]=3)[CH2:27][CH2:26]2)=[CH:14][N:13]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57930198(1-(3-Isopropyl-1,2,4-oxadiazol-5-yl)piperidin-4-yl)methyl methanesulfonateHCID 178504684HCID 178504684, compound

Product 1

HCID 24995589HCID 24995589, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound (0.13 g, 49%) was prepared as a white solid from 5-[2-fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinol (and tautomers thereof) (0.15 g, 0.56 mmol), {1-[3-(1-methylethyl)-1,2,4-oxadiazol-5-yl]-4-piperidinyl}methyl methanesulfonate (prepared as in Example 100, Steps 1-4, 0.23 g, 0.76 mmol) and K2CO3 (0.16 g, 1.12 mmol) in DMF (6 mL) in a manner similar to Example 152, Step 3. The crude product was purified by chromatography on a silica gel column eluted with 50% EtOAc/hexanes to give the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.66 (s, 1H), 8.33 (d, 1H, J=1.0 Hz), 8.23 (t, 1H, J=7.8 Hz), 7.82 (dd, 1H, Ja=8.2 Hz, Jb=1.7 Hz), 7.76 (dd, 1H, Ja=10.2 Hz, Jb=1.6 Hz), 4.40-4.30 (m, 2H), 4.29 (d, 2H, J=6.3 Hz), 3.25-3.10 (m, 2H), 3.09 (s, 3H), 2.98 (septet, 1H, J=7.0 Hz), 2.20-2.05 (m, 1H), 2.05-1.90 (m, 2H), 1.60-1.40 (m, 2H), 1.32 (d, 6H, J=6.8 Hz); LRMS (ESI), m/z 476 (M+H).

Workup

  1. customThe crude product was purified by chromatography on a silica gel column
  2. washeluted with 50% EtOAc/hexanes

Sources & evidence

ORD record
ord-7a04650d9cc040c9931d17df8d86951c
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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