Hexane → N-methoxy-N-methylimidazo[1,2-a]pyridine-7-carboxamide

HRID 341207

Reaction equation

HRID 341207 reaction equation
CO[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[CH:6]=1)=[O:4].[CH3:14][N:15](C)[OH:16].[CH3:18][Al](C)C.CCCCCC>C(Cl)Cl>[CH3:18][O:16][N:15]([CH3:14])[C:3]([C:5]1[CH:10]=[CH:9][N:8]2[CH:11]=[CH:12][N:13]=[C:7]2[CH:6]=1)=[O:4]

Participants

6

Reactant 4

HCID 8058HexaneHCID 27970DimethylhydroxylamineHCID 15096964Methyl imidazo(1,2-a)pyridine-7-carboxylateHCID 16682925Trimethylaluminum

Product 1

HCID 59320928N-methoxy-N-methylimidazo[1,2-a]pyridine-7-carboxamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of Imidazo[1,2-a]pyridine-7-carboxylic acid methyl ester (0.67 g, 3.83 mmol) and dimethylhydroxylamine (0.93 g, 9.57 mmol) in CH2Cl2 (40 ml) at 0° C. was added 2M trimethylaluminium solution in hexane (3.8 ml, 9.57 mmol). The reaction mixture was allowed to warm to room temperature and stirred for 1 h, before being cooled back to 0° C. and quenched with ice. The reaction was filtered and liquid fraction partitioned between CH2Cl2/H2O. The organic layer was separated, dried (MgSO4), filtered and the solvent removed in vacuo to afford the crude product. The residue was purified by silica column chromatography (0-50% MeOH in Et2O) to afford the product (187 mg). MS: [M+H]+=206.

Workup

  1. temperaturebefore being cooled back to 0° C.
  2. customquenched with ice
  3. filtrationThe reaction was filtered
  4. customliquid fraction partitioned between CH2Cl2/H2O
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent removed in vacuo
  9. customto afford the crude product
  10. customThe residue was purified by silica column chromatography (0-50% MeOH in Et2O)

Sources & evidence

ORD record
ord-f187bdd8f00149fabc0c4d5902353323
Source dataset
uspto-grants-2014_11
Patent number
US08895745B2

Linked notes

Loading…