Potassium Carbonate → HCID 67388639, compound

HRID 908476Notes

Reaction equation

HRID 908476 reaction equation
[Br:1][C:2]1[C:3]([C:7]([NH:9][CH3:10])=[O:8])=[N:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH:22]1[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]1)(=O)=O>C(#N)C>[Br:1][C:2]1[C:3]([C:7](=[O:8])[NH:9][CH3:10])=[N:4][N:5]([CH:22]2[CH2:27][CH2:26][N:25]([C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[CH2:24][CH2:23]2)[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178485595HCID 178485595, compound

Product 1

HCID 67388639HCID 67388639, compoundYield 41.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-bromo-N-methyl-1H-pyrazole-3-carboxamide (550 mg), potassium carbonate (579 mg) and tert-butyl 4-methylsulfonyloxypiperidine-1-carboxylate (1081 mg) in acetonitrile (20 mL) were stirred at 90° C. overnight. The mixture was concentrated and the residue was dissolved in ethyl acetate, washed with water, brine dried over magnesium sulfate and concentrated. The crude product was purified by flash chromatography on silica gel eluting with 40 to 70% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford tert-butyl 4-[4-bromo-3-(methylcarbamoyl)pyrazol-1-yl]piperidine-1-carboxylate (436 mg) as a off-white solid. The product gave the following characterizing data: NMR Spectrum: (DMSOd6) 1.42 (s, 9H), 1.79 (dd, 1H), 1.84 (dd, 1H), 1.97-2.05 (m, 2H), 2.71 (d, 3H), 2.91 (bs, 2H), 3.97-4.13 (m, 2H), 4.33-4.43 (m, 1H), 8.05 (q, 1H), 8.15 (s, 1H); Mass spectrum: M+H+ 386-388.

Workup

  1. concentrationThe mixture was concentrated
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washwashed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated
  6. customThe crude product was purified by flash chromatography on silica gel eluting with 40 to 70% ethyl acetate in petroleum ether
  7. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-ac78f6a6e4f14fa1a7f163d18273cf4f
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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