3-Chloro-5-methanesulfonylbenzoic acid → 3-Chloro-5-methanesulfonyl-N-methyl-N-(5-o-tolyl-pyridazin-4-yl)-benzamide

HRID 403401Notes

Reaction equation

HRID 403401 reaction equation
[CH3:1][NH:2][C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[CH:7][N:6]=[N:5][CH:4]=1.[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:25]=1)[C:20]([OH:22])=O>>[Cl:16][C:17]1[CH:18]=[C:19]([CH:23]=[C:24]([S:26]([CH3:29])(=[O:28])=[O:27])[CH:25]=1)[C:20]([N:2]([CH3:1])[C:3]1[C:8]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[CH:7][N:6]=[N:5][CH:4]=1)=[O:22]

Participants

3

Reactant 2

HCID 189525313-Chloro-5-methanesulfonylbenzoic acidHCID 86698485N-methyl-5-o-tolylpyridazin-4-amine

Product 1

HCID 717663783-Chloro-5-methanesulfonyl-N-methyl-N-(5-o-tolyl-pyridazin-4-yl)-benzamideYield 44%

Procedure

The title compound was prepared in analogy to example 1, from methyl-(5-o-tolyl-pyridazin-4-yl)-amine and 3-chloro-5-methanesulfonyl-benzoic acid. A second purification step using preparative HPLC (Gemini NX column) with a gradient of acetonitrile:water with 0.05% formic acid (80:20 to 98:2) gave the desired compound as a colorless solid (44%). MS (ESI+): m/z=416.083 ([M+H]+).

Workup

  1. customA second purification step

Sources & evidence

ORD record
ord-a2037791d59b4132a1d534a00f2d87c6
Source dataset
uspto-grants-2014_06
Patent number
US08748434B2

Reaction notes

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