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

HRID 1746108Notes

Reaction equation

HRID 1746108 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].FC1C=CC=C(F)C=1C(NC1C=NN(CC2C=CC=CC=2COC2C=CC=CC=2)C=1)=O.C(=O)([O-])[O-].[K+].[K+].Br[CH2:55][C:56]1[CH:61]=[CH:60][C:59]([Cl:62])=[CH:58][C:57]=1[O:63][CH2:64][C:65]1[CH:70]=[CH:69][CH:68]=[CH:67][CH:66]=1>CN(C=O)C>[Cl:62][C:59]1[CH:60]=[CH:61][C:56]([CH2:55][N:10]2[CH:11]=[C:7]([NH:6][C:4](=[O:5])[C:3]3[C:2]([F:1])=[CH:15][CH:14]=[CH:13][C:12]=3[F:16])[CH:8]=[N:9]2)=[C:57]([O:63][CH2:64][C:65]2[CH:66]=[CH:67][CH:68]=[CH:69][CH:70]=2)[CH:58]=1

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 434306572,6-Difluoro-N-1H-pyrazol-4-ylbenzamideHCID 569674102,6-Difluoro-N-[1-({2-[(phenyloxy)methyl]phenyl}methyl)-1H-pyrazol-4-yl]benzamideHCID 667254251-(Bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzene

Product 1

HCID 67517266N-[1-({4-Chloro-2-[(phenylmethyl)oxy]phenyl}methyl)-1H-pyrazol-4-yl]-2,6-difluorobenzamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2,6-difluoro-N-1H-pyrazol-4-ylbenzamide (for a preparation see intermediate 2, 52 mg, 0.23 mmol) and potassium carbonate (65 mg, 0.47 mmol) was added a solution of 1-(bromomethyl)-4-chloro-2-[(phenylmethyl)oxy]benzene (74 mg, 0.27 mmol) in DMF (1 ml). The reaction was stirred overnight, under nitrogen and at ambient temperature. The suspension was filtered using a hydrophobic frit and the residue washed with methanol (1 ml). The filtrate was purified by MDAP (Method A) on Supelcosil ABZ+Plus column using acetonitrile-water with a formic acid modifier. The solvent was evaporated in vacuo to give the title compound (33 mg) as a white solid; LCMS (System 1): MH+=454, tRET=3.60 min.

Workup

  1. filtrationThe suspension was filtered
  2. washthe residue washed with methanol (1 ml)
  3. customThe filtrate was purified by MDAP (Method A) on Supelcosil ABZ+Plus column
  4. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-01d2cc3ce5804a8a99308b1c483ed097
Source dataset
uspto-grants-2015_10
Patent number
US09149462B2

Reaction notes

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