Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 86634551, compound

HRID 2387206Notes

Reaction equation

HRID 2387206 reaction equation
[NH2:1][C:2]1[C:3]([C:9]([OH:11])=O)=[N:4][C:5]([Br:8])=[CH:6][N:7]=1.CN([C:15]([O:19][N:20]1N=NC2C=CC=N[C:21]1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.C(N(C(C)C)CC)(C)C.Cl.CONC>CN(C=O)C>[CH3:15][O:19][N:20]([CH3:21])[C:9]([C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([Br:8])[N:4]=1)=[O:11]

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 185216003-Amino-6-bromopyrazine-2-carboxylic acid

Product 1

HCID 86634551HCID 86634551, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 3-amino-6-bromo-pyrazine-2-carboxylic acid (0.62 g, 2.8 mmol), HATU (1.3 g, 3.4 mmol) and di-isopropylethylamine (1.72 ml, 3.5 mmol) in DMF (20 ml) is stirred at room temperature for 5 minutes. N-Methoxy-N-methylamine hydrochloride (0.33 g, 3.4 mmol) is added and the reaction is stirred at room temperature for 2 hours. The solvent is concentrated in vacuo and the residue dissolved in EtOAc (30 ml), and washed with sat. aq. NaHCO3 (20 ml), 0.1N HCl (20 ml), dried (MgSO4) and concentrated in vacuo to yield a brown oil. Purification by flash chromatography (SiO2, 30% EtOAc in iso-hexane) yields 3-amino-6-bromo-pyrazine-2-carboxylic acid methoxy-methyl-amide as a yellow solid [M+H]+ 261.

Workup

  1. concentrationThe solvent is concentrated in vacuo
  2. dissolutionthe residue dissolved in EtOAc (30 ml)
  3. washwashed with sat. aq. NaHCO3 (20 ml), 0.1N HCl (20 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a brown oil
  7. customPurification by flash chromatography (SiO2, 30% EtOAc in iso-hexane)

Sources & evidence

ORD record
ord-7b19864a46bc43ddbc0377f651129e51
Source dataset
uspto-grants-2012_09
Patent number
US08268834B2

Reaction notes

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