Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 11651576, compound

HRID 2370756Notes

Reaction equation

HRID 2370756 reaction equation
[F:1][C:2]([F:13])([F:12])[C:3]1[C:8]([C:9](O)=[O:10])=[CH:7][N:6]=[CH:5][CH:4]=1.Cl.[CH3:15][NH:16][O:17][CH3:18].C(N(C(C)C)C(C)C)C.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>C(Cl)Cl.O>[CH3:18][O:17][N:16]([CH3:15])[C:9](=[O:10])[C:8]1[C:3]([C:2]([F:13])([F:12])[F:1])=[CH:4][CH:5]=[N:6][CH:7]=1

Participants

7

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27775493-Pyridinecarboxylic acid, 4-(trifluoromethyl)-HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 11651576HCID 11651576, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 4-(trifluoromethyl)nicotinic acid (2.11 g, 11.04 mmol) and N,O-dimethylhydroxylamine hydrochloride (1.077 g, 11.04 mmol) in DCM (20 mL) was added N-ethyl-N-isopropylpropan-2-amine (3.78 mL, 22.08 mmol), and HATU (4.20 g, 11.04 mmol). The reaction was stirred at rt under N2 for 5 h. The reaction was then diluted with H2O (50 mL) and extracted with DCM (2×50 mL). The organic layers were combined, dried (MgSO4), and concentrated to give the amide. Purification by ISCO (80 g SiO2, 10-50% EtOAc/hexanes) gives N-methoxy-N-methyl-4-(trifluoromethyl)nicotinamide as a yellow oil.

Workup

  1. extractionextracted with DCM (2×50 mL)
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-f85fe88618f54604b136b782b5ece97f
Source dataset
uspto-grants-2014_04
Patent number
US08710043B2

Reaction notes

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