Methanamine, N-methoxy-, hydrochloride (1:1) → HCID 178502683, compound

HRID 82266

Reaction equation

HRID 82266 reaction equation
[Br:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([OH:9])=O.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.Cl.CONC.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O>[Br:1][C:2]1[C:3]([OH:11])=[N:4][CH:5]=[C:6]([CH:10]=1)[C:7]([N:20]([O:19][CH3:15])[CH3:21])=[O:9]

Participants

7

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 178524767HCID 178524767, compound

Product 1

HCID 178502683HCID 178502683, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

5-Bromo-6-hydroxy-nicotinic acid (Preparation 238, 4 g, 18.4 mmol), HATU (13.95 g, 36.71 mmol), O,N-Dimethyl-hydroxylamine hydrochloride (2.15 g, 22.02 mmol) and DIPEA (15.82 mL, 91.75 mmol) were taken in anhydrous DMF (30 mL). The mixture was stirred at room temperature for 16 hours. The reaction mixture was diluted with EtOAc (150 mL), washed with saturated aq. Na2CO3 (2×50 mL), water (4×30 mL), brine (30 mL), dried (Na2SO4) and evaporated in vacuo. The crude mixture was purified by column chromatography on silica gel (gradient of EtOAc:Hex 4:6 to 6:4) to afford the title compound as light yellow sticky solid in 38%, 1.8 g.

Workup

  1. washwashed with saturated aq. Na2CO3 (2×50 mL), water (4×30 mL), brine (30 mL)
  2. dry with materialdried (Na2SO4)
  3. customevaporated in vacuo
  4. customThe crude mixture was purified by column chromatography on silica gel (gradient of EtOAc:Hex 4:6 to 6:4)

Sources & evidence

ORD record
ord-1240e203e19144038d94a0a8e0b1e77a
Source dataset
uspto-grants-2014_09
Patent number
US08846698B2

Linked notes

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