3,5-Bis(trifluoromethyl)benzoic acid → N-(6-Chloro-4-phenyl-pyridazin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

HRID 403384Notes

Reaction equation

HRID 403384 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([NH:8][CH3:9])=[C:4]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[CH:3]=1.[F:16][C:17]([F:32])([F:31])[C:18]1[CH:19]=[C:20]([CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=1)[C:21]([OH:23])=O>CCCCCCC.C(OCC)(=O)C>[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]([CH3:9])[C:21](=[O:23])[C:20]2[CH:24]=[C:25]([C:27]([F:30])([F:29])[F:28])[CH:26]=[C:18]([C:17]([F:16])([F:32])[F:31])[CH:19]=2)=[C:4]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 128893,5-Bis(trifluoromethyl)benzoic acidHCID 866984786-chloro-N-methyl-4-phenylpyridazin-3-amine

Product 1

HCID 71766226N-(6-Chloro-4-phenyl-pyridazin-3-yl)-N-methyl-3,5-bis-trifluoromethyl-benzamide

Reagents, catalysts & solvents 1

HCID 21899848Ethylacetate heptaneSolvent

Procedure

The title compound was prepared in analogy to example 1, from (6-chloro-4-phenyl-pyridazin-3-yl)-methyl-amine (example 5, intermediate a) and 3,5-bis(trifluoromethyl)benzoic acid (CAS RN 725-89-3) and using a gradient of n-heptane:ethyl acetate (100:0 to 30:70) for the chromatographic purification. Another purification step using preparative HPLC (Gemini NX column) with a gradient of methanol:water with 0.05% formic acid (80:20 to 98:2) yielded the compound as a colorless solid (5%). MS (ESI+): m/z=460.064 ([M+H]+).

Workup

  1. customfor the chromatographic purification
  2. customAnother purification step

Sources & evidence

ORD record
ord-afe5ec69d94b47b4b52ce27853dcb7b8
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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