Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 59436141, compound

HRID 1805572Notes

Reaction equation

HRID 1805572 reaction equation
Cl.[CH3:2][O:3][C:4]1[C:5](=[O:19])[C:6]([C:16]([OH:18])=O)=[N:7][N:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[CH:9]=1.Cl.[CH3:21][NH:22][O:23][CH3:24].F[B-](F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2C=CC=CC=2N=N1>CN(C=O)C.CCOC(C)=O>[CH3:24][O:23][N:22]([CH3:21])[C:16]([C:6]1[C:5](=[O:19])[C:4]([O:3][CH3:2])=[CH:9][N:8]([C:10]2[CH:11]=[N:12][CH:13]=[CH:14][CH:15]=2)[N:7]=1)=[O:18]

Participants

6

Reactant 3

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 2733207O-(Benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborateHCID 66710601HCID 66710601, compound

Product 1

HCID 59436141HCID 59436141, compoundYield 79.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 5-methoxy-4-oxo-1-pyridin-3-yl-1,4-dihydropyridazine-3-carboxylic acid hydrochloride (1.0 g, 3.5 mmol), N,O-dimethylhydroxylamine hydrochloride (0.52 g, 5.3 mmol), TEA (1.5 ml, 11 mmol) and O-benzotriazol-1-yl-N,N,N′,N′-tetramethyluronium tetrafluoroborate (1.2 g, 3.9 mmol) in DMF (15 ml) was stirred at room temperature overnight. The mixture was diluted with AcOEt. The precipitate was filtered off and the filtrate was concentrated under reduced pressure. The residue was chromatographed on basic silica gel (0/100-20/80 MeOH/AcOEt) to give the title compound (0.81 g, 79% yield) as white crystals: 1H NMR (300 MHz, CDCl3): δ ppm 3.41 (3H, s), 3.71 (3H, s), 3.98 (3H, s), 7.48 (1H, dd, J=8.3, 4.5 Hz), 7.97 (1H, s), 8.00-8.05 (1H, m), 8.67 (1H, dd, J=4.5, 1.3 Hz), 8.91 (1H, d, J=2.6 Hz).

Workup

  1. filtrationThe precipitate was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was chromatographed on basic silica gel (0/100-20/80 MeOH/AcOEt)

Sources & evidence

ORD record
ord-c10c62ca03f7424288da9dc874b59921
Source dataset
uspto-grants-2013_01
Patent number
US08354411B2

Reaction notes

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