Methanamine, N-methoxy-, hydrochloride (1:1) → N-methoxy-N,1-dimethyl-1H-pyrazole-5-carboxamide

HRID 238376Notes

Reaction equation

HRID 238376 reaction equation
Cl.[CH3:2][NH:3][O:4][CH3:5].[CH3:6][N:7]1[C:11]([C:12]([OH:14])=O)=[CH:10][CH:9]=[N:8]1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1.C(N(C(C)C)CC)(C)C>O.CN(C)C=O>[CH3:5][O:4][N:3]([CH3:2])[C:12]([C:11]1[N:7]([CH3:6])[N:8]=[CH:9][CH:10]=1)=[O:14]

Participants

7

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 6431581-methyl-1H-pyrazole-5-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 62038410N-methoxy-N,1-dimethyl-1H-pyrazole-5-carboxamideYield 63.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

N,O-dimethylhydroxylamine hydrochloride (1.30 g) was added to an dimethylformamide (32 mL) solution that contained 1-methyl-1H-pyrazol-5-carboxylic acid (1.21 g), O-(7-azabenzotriazol-1-yl)-N,N,N′,N′-tetramethyluronium hexafluorophosphate (4.38 g) and diisopropylethylamine (3.34 mL) at a room temperature, and the obtained solution was then stirred for 2 hours. Thereafter, water was added to the reaction solution, and the obtained mixture was then extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration. The residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=100:0 to 95:5), so as to obtain the title compound (1.03 g) in the form of a yellow oily substance.

Workup

  1. customat a room temperature
  2. extractionthe obtained mixture was then extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated saline, and was then dried over anhydrous magnesium sulfate
  5. concentrationfollowed by vacuum concentration
  6. customThe residue was purified by column chromatography (silica gel cartridge, chloroform:methanol=100:0 to 95:5)

Sources & evidence

ORD record
ord-01aaea0725f54f8e882d584f78333ee0
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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