Methanamine, N-methoxy-, hydrochloride (1:1) → N-methoxy-N-methylquinoxaline-6-carboxamide

HRID 1771147Notes

Reaction equation

HRID 1771147 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([OH:13])=O)=[CH:8][CH:9]=2)[N:4]=[CH:3][CH:2]=1.CN([C:17]([O:21][N:22]1N=NC2C=CC=N[C:23]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.Cl.CONC>CN(C=O)C>[CH3:17][O:21][N:22]([CH3:23])[C:11]([C:7]1[CH:6]=[C:5]2[C:10](=[CH:9][CH:8]=1)[N:1]=[CH:2][CH:3]=[N:4]2)=[O:13]

Participants

6

Reactant 4

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 674813Quinoxaline-6-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 59208155N-methoxy-N-methylquinoxaline-6-carboxamideYield 80.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of quinoxaline-6-carboxylic acid (5.1 g, 29.3 mmol, 1.0 eq) in DMF (100 mL) were added HATU (13.3 g, 35 mmol. 1.2 eq), DIEA (20 mL, 117.2 mmol, 4.0 eq) and O,N-Dimethyl-hydroxylamine hydrochloride salt (3.38 g, 35 mmol, 1.2 eq). The mixture was stirred at rt overnight, then the solvent was concentrated. The residue was purified via flash column (PE/EA=2/1, v/v) to afford N-methoxy-N-methylquinoxaline-6-carboxamide as a yellow solid (5.1 g, 80%).

Workup

  1. concentrationthe solvent was concentrated
  2. customThe residue was purified via flash column (PE/EA=2/1

Sources & evidence

ORD record
ord-c2b69b45558b4611b334a89291028c92
Source dataset
uspto-grants-2016_02
Patent number
US09249111B2

Reaction notes

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