4-Methylmorpholine → N-(3-fluoro-4-methanesulfonylaminobenzyl)-3-(2-methyl-6-trifluoromethylpyridin-3-yl)acrylamide

HRID 2265991Notes

Reaction equation

HRID 2265991 reaction equation
Cl.[F:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:6][NH2:7].CN1CCOCC1.[CH3:23][C:24]1[C:29]([CH:30]=[CH:31][C:32](O)=[O:33])=[CH:28][CH:27]=[C:26]([C:35]([F:38])([F:37])[F:36])[N:25]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C1COCC1>[F:2][C:3]1[CH:4]=[C:5]([CH:8]=[CH:9][C:10]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH2:6][NH:7][C:32](=[O:33])[CH:31]=[CH:30][C:29]1[C:24]([CH3:23])=[N:25][C:26]([C:35]([F:36])([F:37])[F:38])=[CH:27][CH:28]=1

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 21097525N-[4-(aminomethyl)-2-fluorophenyl]methanesulfonamide hydrochlorideHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 685099343-(2-Methyl-6-trifluoromethylpyridin-3-yl)acrylic acid

Product 1

HCID 68782220N-(3-fluoro-4-methanesulfonylaminobenzyl)-3-(2-methyl-6-trifluoromethylpyridin-3-yl)acrylamideYield 58.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 3-fluoro-4-methansulfonylaminobenzylamine hydrochloride (67 mg, 0.26 mmol) in THF (5 mL) was added N-methylmorpholine (43 μL, 0.39 mmol). After stirring for 5 minutes, 3-(2-methyl-6-trifluoromethylpyridin-3-yl)acrylic acid (60 mg, 0.26 mmol) and 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMTMM, 73 mg, 0.26 mmol) were added. The mixture was stirred at room temperature overnight, concentrated under reduced pressure, and diluted with EtOAc and water. The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The crude product was purified by recrystallization from EtOAc/hexane to give N-(3-fluoro-4-methanesulfonylaminobenzyl)-3-(2-methyl-6-trifluoromethylpyridin-3-yl)acrylamide (66 mg, 58.8%) as a solid.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationconcentrated under reduced pressure
  3. additiondiluted with EtOAc and water
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe crude product was purified by recrystallization from EtOAc/hexane

Sources & evidence

ORD record
ord-4c57844780a94c3a93efd0699187b878
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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