Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 57762806, compound

HRID 230647

Reaction equation

HRID 230647 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.[CH3:25][N:26]1[CH:30]=[CH:29][N:28]=[C:27]1[C:31]([OH:33])=O.Cl.CNOC.C(N(C(C)C)CC)(C)C>CN(C=O)C>[CH3:10][N:9]([O:8][CH3:4])[C:31]([C:27]1[N:26]([CH3:25])[CH:30]=[CH:29][N:28]=1)=[O:33]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 5576781-methyl-1H-imidazole-2-carboxylic 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 57762806HCID 57762806, compoundYield 212.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

HATU (O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate) (1.75 g; 4.60 mmol) was added in on portion to a stirring solution of 1-methyl-1H-imidazole-2-carboxylic acid (509 mg; 4.04 mmol), N,O-dimethylhydroxylamine hydrochloride (391 mg; 4.01 mmol), and diisopropylethylamine (2.0 mL; 11.9 mmol) in anhydrous DMF (14 mL). The mixture was stirred at room temperature for 17 hours and partitioned between ethyl acetate (100 mL) and water (100 mL). The organic phase was dried (MgSO4) and concentrated in vacuo, giving a colourless oil (1.45 g). This was purified by column chromatography, giving the title compound as a colourless oil (494 mg; 73%).

Workup

  1. custompartitioned between ethyl acetate (100 mL) and water (100 mL)
  2. dry with materialThe organic phase was dried (MgSO4)
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1b057176fc3b4694a4209927e8cc5045
Source dataset
uspto-grants-2009_07
Patent number
US07566735B2

Linked notes

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