Potassium Carbonate → HCID 59177742, compound

HRID 423642Notes

Reaction equation

HRID 423642 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]=[CH:13][C:14]([OH:17])=[N:15][CH:16]=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]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]1)[CH3:24])(=O)=O.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]=[CH:13][C:14]([O:17][CH:23]([CH:25]3[CH2:26][CH2:27][N:28]([C:31]([O:33][C:34]([CH3:35])([CH3:37])[CH3:36])=[O:32])[CH2:29][CH2:30]3)[CH3:24])=[N:15][CH:16]=2)=[CH:9][CH:10]=1)(=[O:3])=[O:4]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 232828864-[1-[(Methylsulfonyl)oxy]ethyl]-1-piperidinecarboxylic acid 1,1-dimethylethyl esterHCID 178504683HCID 178504683, compound

Product 1

HCID 59177742HCID 59177742, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound (0.463 g, 58%) was prepared as a white foam from 5-[4-(methylsulfonyl)phenyl]-2-pyrazinol (and tautomers thereof) (prepared as in Example 145, Step 2, 0.43 g, 1.72 mmol), (±)-1,1-dimethylethyl 4-{1-[(methylsulfonyl)oxy]ethyl}-1-piperidinecarboxylate (0.74 g, 2.41 mmol) and K2CO3 (0.48 g, 3.44 mmol) in DMF (15 mL) in a manner similar to Example 150, Step 3. The crude product was purified by chromatography on a silica gel column eluted with 1:2 EtOAc/hexanes then 40% EtOAc/hexanes to give the title compound as a white foam. 1H NMR (400 MHz, CDCl3): δ 8.53 (s, 1H), 8.24 (s, 1H), 8.10 (d, 2H, J=8.3 Hz), 8.02 (d, 2H, J=8.3 Hz), 5.15-5.05 (m, 1H), 4.20-4.10 (m, 2H), 3.07 (s, 3H), 2.75-2.60 (m, 2H), 1.85-1.55 (m, 3H), 1.44 (s, 9H), 1.40-1.20 (m, 5H); LRMS (ESI), m/z 462 (M+H).

Workup

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

Sources & evidence

ORD record
ord-6cfff20c1e2c45ac92b37b02129ec29d
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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