Methanamine, N-methoxy-, hydrochloride (1:1) → 4,4-Difluoro-N-methoxy-N-methylcyclohexanecarboxamide

HRID 406030Notes

Reaction equation

HRID 406030 reaction equation
CN([C:4]([O:8][N:9]1N=NC2C=CC=N[C:10]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:25][C:26]1([F:35])[CH2:31][CH2:30][CH:29]([C:32](O)=[O:33])[CH2:28][CH2:27]1.C(N(C(C)C)CC)(C)C.Cl.CONC>CN(C=O)C>[CH3:4][O:8][N:9]([CH3:10])[C:32]([CH:29]1[CH2:30][CH2:31][C:26]([F:35])([F:25])[CH2:27][CH2:28]1)=[O:33]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 27791364,4-Difluorocyclohexanecarboxylic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Product 1

HCID 584217634,4-Difluoro-N-methoxy-N-methylcyclohexanecarboxamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2.78 g HATU were added to a solution of 1 g 4,4-difluoro-cyclohexanecarboxylic acid and 1.3 ml diisopropylethlyamine in 10 ml anhydrous DMF at 0° C. The reaction was stirred at 0° C. for 0.5 hours when 0.891 g O,N-Dimethyl-hydroxylamine hydrochloride were added. The reaction was allowed to warm to rt overnight. The solution was concentrated in vacuo by co-evaporation with toluene (3×) and filtered. The filtrate was concentrated in vacuo. Purification was achieved by silica gel column chromatography (solvent: 5:1→3:1 petroleum ether/EtOAc).

Workup

  1. additionwere added
  2. concentrationThe solution was concentrated in vacuo by co-evaporation with toluene (3×)
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated in vacuo
  5. customPurification

Sources & evidence

ORD record
ord-3cb0cbca815b4d70b735c150f5551337
Source dataset
uspto-grants-2014_06
Patent number
US08754079B2

Reaction notes

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