Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 117601942, compound

HRID 1773727Notes

Reaction equation

HRID 1773727 reaction equation
[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]2[C:13]([CH3:18])=[N:14][O:15][C:16]=2[CH3:17])=[CH:7][C:3]=1[C:4]([OH:6])=O.CN([C:22]([O:26][N:27]1N=NC2C=CC=N[C:28]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CNOC>CN(C=O)C>[NH2:1][C:2]1[C:10]([NH2:11])=[CH:9][C:8]([C:12]2[C:13]([CH3:18])=[N:14][O:15][C:16]=2[CH3:17])=[CH:7][C:3]=1[C:4]([N:27]([O:26][CH3:22])[CH3:28])=[O:6]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 117601746HCID 117601746, compound

Product 1

HCID 117601942HCID 117601942, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2,3-diamino-5-(3,5-dimethylisoxazol-4-yl)benzoic acid (22 g, 0.089 mol) was dissolved in DMF (C=3.0 M) and HATU (1.3 eq), DIPEA (7 eq), and N,O-dimethylhydroxylamine hydrochloride (2.5 eq) were added in one portion and the reaction was allowed to stir under air at room temperature for 1 hr. The reaction was concentrated in vacuo and the residue was dissolved in ethyl acetate. The solution was washed once with NaHCO3 and three times with brine. The crude was concentrated in vacuo and purified via silica gel chromatography to give 2,3-diamino-5-(3,5-dimethylisoxazol-4-yl)-N-methoxy-N-methylbenzamide as a light brown powder.

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. dissolutionthe residue was dissolved in ethyl acetate
  3. washThe solution was washed once with NaHCO3 and three times with brine
  4. concentrationThe crude was concentrated in vacuo
  5. custompurified via silica gel chromatography

Sources & evidence

ORD record
ord-759e4afb3f074d149cd5bc83c8a7492a
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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