Potassium Carbonate → HCID 67389074, compound

HRID 908477Notes

Reaction equation

HRID 908477 reaction equation
[Br:1][C:2]1[C:3]([C:7]([NH2:9])=[O:8])=[N:4][NH:5][CH:6]=1.C(=O)([O-])[O-].[K+].[K+].CS(O[CH:21]1[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]1)(=O)=O>C(#N)C>[Br:1][C:2]1[C:3]([C:7](=[O:8])[NH2:9])=[N:4][N:5]([CH:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[CH2:23][CH2:22]2)[CH:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 41848691-(tert-Butoxycarbonyl)-4-(methanesulfonyloxy)piperidineHCID 178513845HCID 178513845, compound

Product 1

HCID 67389074HCID 67389074, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-bromo-1H-pyrazole-3-carboxamide (673 mg), potassium carbonate (636 mg) and tert-butyl 4-methylsulfonyloxypiperidine-1-carboxylate (1187 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 55 to 100% ethyl acetate in petroleum ether. The solvent was evaporated to dryness to afford tert-butyl 4-(4-bromo-3-carbamoyl-pyrazol-1-yl)piperidine-1-carboxylate (489 mg) as a solid. NMR Spectrum: (DMSOd6): 1.41 (s, 9H), 1.78 (dd, 1H), 1.83 (dd, 1H), 1.96-2.04 (m, 2H), 2.90 (bs, 2H), 4.03 (m, 2H), 4.33-4.41 (m, 1H), 7.30 (s, 1H), 7.44 (s, 1H), 8.14 (s, 1H)

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 55 to 100% ethyl acetate in petroleum ether
  7. customThe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-72d8b2f1d7524d4cba2fdc83afcfdccd
Source dataset
uspto-grants-2011_09
Patent number
US08017611B2

Reaction notes

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