4-Methylmorpholine → HCID 59598164, compound

HRID 2265955Notes

Reaction equation

HRID 2265955 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].Cl.[CH3:16][NH:17][O:18][CH3:19].CN1CCOCC1.Cl.CN(C)CCCN=C=NCC>C(Cl)Cl.CCOC(C)=O.O>[Cl:1][C:2]1[N:10]=[C:9]([C:11]([F:14])([F:13])[F:12])[CH:8]=[CH:7][C:3]=1[C:4]([N:17]([O:18][CH3:19])[CH3:16])=[O:5]

Participants

8

Reactant 4

HCID 79724-MethylmorpholineHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27782102-Chloro-6-(trifluoromethyl)nicotinic acid

Product 1

HCID 59598164HCID 59598164, compoundYield 93.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 2-chloro-6-trifluoromethyl-nicotinic acid (200 mg, 0.88 mmol) and N,O-dimethylhydroxylamine hydrochloride (95 mg, 0.97 mmol) in CH2Cl2 (3 mL) was added N-methylmorpholine (0.106 ml, 0.97 mmol). The mixture was stirred for 5 minutes, to which was added N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide hydrochloride (185 mg, 0.97 mmol). The mixture was stirred for 3 hours at room temperature, and then diluted with EtOAc and water. The organic layer was washed with 1N HCl, saturated sodium bicarbonate and brine, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The product was vacuum dried to yield the 2-chloro-N-methoxy-N-methyl-6-trifluoromethyl-nicotinamide (220 mg, 92%).

Workup

  1. stirringThe mixture was stirred for 3 hours at room temperature
  2. washThe organic layer was washed with 1N HCl, saturated sodium bicarbonate and brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customdried

Sources & evidence

ORD record
ord-e36cb31824e343c79de4e636f00caf93
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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