4-Methylmorpholine → HCID 72335659, compound

HRID 2265966Notes

Reaction equation

HRID 2265966 reaction equation
Cl.[C:2]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([F:17])[C:11]=1[NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:7][NH2:8])#[CH:3].CN1CCOCC1.[CH3:25][O:26][C:27]1[N:32]=[CH:31][C:30]([CH:33]=[CH:34][C:35](O)=[O:36])=[C:29]([C:38]([F:41])([F:40])[F:39])[CH:28]=1.O.[Cl-].COC1N=C(OC)N=C([N+]2(C)CCOCC2)N=1>C1COCC1>[C:2]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([F:17])[C:11]=1[NH:12][S:13]([CH3:16])(=[O:15])=[O:14])[CH2:7][NH:8][C:35](=[O:36])[CH:34]=[CH:33][C:30]1[CH:31]=[N:32][C:27]([O:26][CH3:25])=[CH:28][C:29]=1[C:38]([F:40])([F:39])[F:41])#[CH:3]

Participants

6

Reactant 4

HCID 79724-MethylmorpholineHCID 231494114-(4,6-Dimethoxy[1.3.5]triazin-2-yl)-4-methylmorpholinium chloride hydrateHCID 68781732HCID 68781732, compoundHCID 866255193-Ethynyl-5-fluoro-4-methansulfonylaminobenzylamine hydrochloride

Product 1

HCID 72335659HCID 72335659, compoundYield 79.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of 3-ethynyl-5-fluoro-4-methansulfonylaminobenzylamine hydrochloride (67 mg, 0.24 mmol) m THF (2 mL) was added N-methylmorpholine (40 μL, 0.36 mmol). After stirring for 5 minutes, 3-(6-methoxy-4-trifluoromethylpyridin-3-yl)acrylic acid (50 mg, 0.20 mmol) dissolved in THF (3 mL) and 4-(4,6-dimethoxy[1,3,5]triazin-2-yl)-4-methylmorpholinium chloride hydrate (DMTMM, 67 mg, 0.24 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-ethynyl-5-fluoro-4-methanesulfonylaminobenzyl)-3-(6-methoxy-4-trifluoromethylpyridin-3-yl)acrylamide (75 mg, 66.2%) 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-99f265c09ff94ab7b472f2dc2a7c9ac2
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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