Potassium Carbonate → 1-Methylethyl 4-[({5-[2-fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)methyl]-1-piperidinecarboxylate

HRID 423653Notes

Reaction equation

HRID 423653 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]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[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[N:13]=[CH:14][C:15]([O:18][CH2:24][CH:25]2[CH2:30][CH2:29][N:28]([C:31]([O:33][CH:34]([CH3:36])[CH3:35])=[O:32])[CH2:27][CH2:26]2)=[N:16][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 57930057Isopropyl 4-((methylsulfonyloxy)methyl)piperidine-1-carboxylateHCID 178504684HCID 178504684, compound

Product 1

HCID 591777751-Methylethyl 4-[({5-[2-fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinyl}oxy)methyl]-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound (80 mg, 49%) was prepared as a white solid from 5-[2-fluoro-4-(methylsulfonyl)phenyl]-2-pyrazinol (and tautomers thereof) (prepared as in Example 161, Step 2, 98 mg, 0.37 mmol), 1-methylethyl 4-{[(methylsulfonyl)oxy]methyl}-1-piperidinecarboxylate (prepared as in Example 131, Step 4, 0.138 g, 0.49 mmol) and K2CO3 (0.102 g, 0.73 mmol) in DMF (4 mL) in a manner similar to Example 152, Step 3. The crude product was purified by chromatography on an ISCO silica gel column using 0 to 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=1.3 Hz), 8.23 (t, 1H, J=7.8 Hz), 7.85-7.70 (m, 2H), 4.91 (septet, 1H, J=6.2 Hz), 4.30-4.15 (m, 4H), 3.09 (s, 3H), 2.85-2.70 (m, 2H), 2.10-1.95 (m, 1H), 1.85-1.75 (m, 2H), 1.35-1.20 (m, 8H); LRMS (ESI), m/z 452 (M+H).

Workup

  1. customThe crude product was purified by chromatography on an ISCO silica gel column

Sources & evidence

ORD record
ord-abb127b4657d4902a84a5b5f19b69def
Source dataset
uspto-grants-2012_01
Patent number
US08101634B2

Reaction notes

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