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Ammonium Chloride → N-[5-(4-Fluoro-2-methoxy-phenyl)-pyridazin-4-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide

HRID 403395
Notes
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Reaction equation

HRID 403395 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([NH:14][CH3:15])=[CH:10][N:11]=[N:12][CH:13]=2)=[C:4]([O:16][CH3:17])[CH:3]=1.[CH3:18][S:19]([C:22]1[CH:23]=[C:24]([CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=1)[C:25](Cl)=[O:26])(=[O:21])=[O:20].C(N(CC)C(C)C)(C)C.[Cl-].[NH4+]>ClCCl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([N:14]([CH3:15])[C:25](=[O:26])[C:24]3[CH:28]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:30]=[C:22]([S:19]([CH3:18])(=[O:21])=[O:20])[CH:23]=3)=[CH:10][N:11]=[N:12][CH:13]=2)=[C:4]([O:16][CH3:17])[CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 81531DiisopropylethylamineHCID 866708083-(Methylsulfonyl)-5-(trifluoromethyl)benzoyl chlorideHCID 866984835-(4-fluoro-2-methoxyphenyl)-N-methylpyridazin-4-amine

Product 1

HCID 71766376N-[5-(4-Fluoro-2-methoxy-phenyl)-pyridazin-4-yl]-3-methanesulfonyl-N-methyl-5-trifluoromethyl-benzamide
Yield 26.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(4-fluoro-2-methoxyphenyl)-N-methylpyridazin-4-amine (27 mg, 116 μmol) in dichloromethane (1 mL) were added 3-(methylsulfonyl)-5-(trifluoromethyl)benzoyl chloride (66.4 mg, 232 mmol) and N,N-diisopropylethylamine (60 mg, 80.9 μL, 463 μmol). The clear, light brown solution was stirred at room temperature for 1.75 h and then poured on saturated aqueous ammonium chloride solution and dichloromethane and the layers were separated. The aqueous layer was extracted three times with dichloromethane. The organic layers were dried over magnesium sulfate, filtered, treated with silica gel and evaporated. The compound was purified by silica gel chromatography on a 10 g column using a MPLC system (CombiFlash Companion, Isco Inc.) eluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100) to give the desired compound as a light brown solid (15 mg; 25%). MS (ESI+): m/z=483.09 ([M+H]+).

Workup

  1. customthe layers were separated
  2. extractionThe aqueous layer was extracted three times with dichloromethane
  3. dry with materialThe organic layers were dried over magnesium sulfate
  4. filtrationfiltered
  5. additiontreated with silica gel
  6. customevaporated
  7. customThe compound was purified by silica gel chromatography on a 10 g column
  8. washeluting with a gradient of n-heptane:ethyl acetate (100:0 to 0:100)

Sources & evidence

ORD record
ord-2b52fa2986fa44508a31d6cb3482726e
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748434B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes