2,6-Dichlorobenzoic acid → 2,6-Dichloro-N-{1-[(2,4-dichlorophenyl)methyl]-1H-pyrazol-4-yl}benzamide

HRID 1746109Notes

Reaction equation

HRID 1746109 reaction equation
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[Cl:25][C:26]1[CH:34]=[CH:33][CH:32]=[C:31]([Cl:35])[C:27]=1[C:28]([OH:30])=O.CCN(C(C)C)C(C)C.[Cl:45][C:46]1[CH:51]=[C:50]([Cl:52])[CH:49]=[CH:48][C:47]=1[CH2:53][N:54]1[CH:58]=[C:57]([NH2:59])[CH:56]=[N:55]1>CN(C=O)C>[Cl:35][C:31]1[CH:32]=[CH:33][CH:34]=[C:26]([Cl:25])[C:27]=1[C:28]([NH:59][C:57]1[CH:56]=[N:55][N:54]([CH2:53][C:47]2[CH:48]=[CH:49][C:50]([Cl:52])=[CH:51][C:46]=2[Cl:45])[CH:58]=1)=[O:30]

Participants

6

Reactant 4

HCID 57582,6-Dichlorobenzoic acidHCID 81531DiisopropylethylamineHCID 5945001-(2,4-dichlorobenzyl)-1H-pyrazol-4-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 569674692,6-Dichloro-N-{1-[(2,4-dichlorophenyl)methyl]-1H-pyrazol-4-yl}benzamideYield 76.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of HATU (46 mg, 0.12 mmol) in DMF (200 μl) was added to 2,6-dichlorobenzoic acid (22 mg, 0.11 mmol, Avocado) followed by DIPEA (50 μl, 0.286 mmol) and left to stand for 5 min at ambient temperature. A solution of 1-[(2,4-dichlorophenyl)methyl]-1H-pyrazol-4-amine (Art Chem GmbH; 53 mg, 0.22 mmol) in DMF (200 μl) was then added and the solution left to stand for 16 h at ambient temperature. The solvent was removed using a Genevac. The sample was dissolved in 1:1 MeOH:DMSO (0.6 ml) and purified by MDAP on a standard C18 column (method D) using acetonitrile-water with a TFA modifier. The solvent was evaporated in vacuo using a Genevac to give the title compound (35 mg); LCMS (System 3): MH+=414, tRET=1.18 min.

Workup

  1. waitleft
  2. waitthe solution left
  3. waitto stand for 16 h at ambient temperature
  4. customThe solvent was removed
  5. dissolutionThe sample was dissolved in 1:1 MeOH
  6. customDMSO (0.6 ml) and purified by MDAP on a standard C18 column (method D)
  7. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-76dddeb729d34832b46852e3979c5f37
Source dataset
uspto-grants-2015_10
Patent number
US09149462B2

Reaction notes

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