4-Methylmorpholine → HCID 68785427, compound

HRID 2265968Notes

Reaction equation

HRID 2265968 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][O:24][C:25]1[N:30]=[CH:29][C:28]([CH:31]=[CH:32][C:33](O)=[O:34])=[C:27]([C:36]([F:39])([F:38])[F:37])[CH:26]=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:33](=[O:34])[CH:32]=[CH:31][C:28]1[CH:29]=[N:30][C:25]([O:24][CH3:23])=[CH:26][C:27]=1[C:36]([F:38])([F:37])[F:39]

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 68781732HCID 68781732, compound

Product 1

HCID 68785427HCID 68785427, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3-fluoro-4-methansulfonylaminobenzylamine hydrochloride (40 mg, 0.16 mmol) in THF (4 mL) was added N-methylmorpholine (26 μL, 0.24 mmol). After stirring for 5 minutes, 3-[6-methoxy-4-(trifluoromethyl)pyridin-3-yl]acrylic acid (32 mg, 0.13 mmol) dissolved in THF (3 mL) and 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMTMM, 43 mg, 0.16 mmol) were added. The mixture was stirred at room temperature overnight and concentrated under reduced pressure. The residue was 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-(6-methoxy-4-trifluoromethylpyridin-3-yl)acrylamide (30 mg, 42.7%) as a solid.

Workup

  1. stirringThe mixture was stirred at room temperature overnight
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted 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-2193420fb1dd4f82b2ba19dda2dcecb6
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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