4-Methylmorpholine → 1049025-94-6

HRID 909665Notes

Reaction equation

HRID 909665 reaction equation
[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([OH:10])=O)=[N:6][CH:7]=1.C1C=CC2N(O)N=[N:17][C:15]=2C=1.CCN=C=NCCCN(C)C.Cl.CN1CCOCC1.CN.CO>CN(C)C=O.O>[Cl:1][C:2]1[N:3]=[CH:4][C:5]([C:8]([NH:17][CH3:15])=[O:10])=[N:6][CH:7]=1

Participants

8

Reactant 5

HCID 79724-MethylmorpholineHCID 757711-HydroxybenzotriazoleHCID 4654725-Chloropyrazinoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 57454252Monomethylamine methanol

Product 1

HCID 592769911049025-94-6Yield 27%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

5-Chloropyrazine-2-carboxylic acid (1.99 g, 12.6 mmol) was dissolved in N,N-dimethylformamide (10 mL), and HOBt.H2O (591 mg, 3.86 mmol), WSCI•HCl (1.35 g, 7.02 mmol), N-methylmorpholine (2.76 mL, 25.1 mmol) and 40% methylamine/methanol solution (2.92 mL, 37.6 mmol) were added, followed by stirring for 18 hours. To the reaction solution, water (50 mL) was added, and extraction was carried out twice with ethyl acetate (50 mL). The organic layer was washed with saturated brine, and subsequently dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified using silica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-75%) to afford the desired compound (585 mg, yield 27%) as a white solid.

Workup

  1. extractionextraction
  2. washThe organic layer was washed with saturated brine
  3. dry with materialsubsequently dried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off under reduced pressure
  5. customthe resulting residue was purified
  6. washsilica gel column chromatography (elution solvent: ethyl acetate/hexane=0%-75%)

Sources & evidence

ORD record
ord-9834604f40d7450487ce2a92ade228f9
Source dataset
uspto-grants-2011_09
Patent number
US08017610B2

Reaction notes

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