Potassium Carbonate → N-(1-{[2-(Butyloxy)phenyl]methyl}-1H-pyrazol-4-yl)-2,6-difluorobenzamide

HRID 1746106Notes

Reaction equation

HRID 1746106 reaction equation
[F:1][C:2]1[CH:15]=[CH:14][CH:13]=[C:12]([F:16])[C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[N:9][NH:10][CH:11]=1)=[O:5].Br[CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[O:25][CH2:26][CH2:27][CH2:28][CH3:29].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[CH2:26]([O:25][C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=1[CH2:18][N:10]1[CH:11]=[C:7]([NH:6][C:4](=[O:5])[C:3]2[C:2]([F:1])=[CH:15][CH:14]=[CH:13][C:12]=2[F:16])[CH:8]=[N:9]1)[CH2:27][CH2:28][CH3:29]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 201948961-(Bromomethyl)-2-butoxybenzeneHCID 434306572,6-Difluoro-N-1H-pyrazol-4-ylbenzamide

Product 1

HCID 56967409N-(1-{[2-(Butyloxy)phenyl]methyl}-1H-pyrazol-4-yl)-2,6-difluorobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,6-Difluoro-N-1H-pyrazol-4-ylbenzamide (for a preparation see intermediate 2, 45 mg, 0.20 mmol), 1-(bromomethyl)-2-(butyloxy)benzene (for a preparation see intermediate 4, 56 mg, 0.23 mmol) and potassium carbonate (42 mg, 0.30 mmol) were weighed into a vial with a stirrer. DMF (0.5 ml) was added, the vial was capped and the mixture was stirred at ambient temperature for 26 h. The reaction mixture was filtered, washing with MeOH to give a total volume of 1 ml. This solution was purified by MDAP Sunfire C18 column (Method B) using acetonitrile-water with a formic acid modifier. The solvent was removed to give the title compound (25 mg) as a colourless gum; LCMS (System 4): MH+=386, tRET=3.02 min.

Workup

  1. customthe vial was capped
  2. filtrationThe reaction mixture was filtered
  3. washwashing with MeOH
  4. customto give a total volume of 1 ml
  5. customThis solution was purified by MDAP Sunfire C18 column (Method B)
  6. customThe solvent was removed

Sources & evidence

ORD record
ord-00ca07f4db454d228dd2209681ec28b1
Source dataset
uspto-grants-2015_10
Patent number
US09149462B2

Reaction notes

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