Methylamine → HCID 86714140, compound

HRID 919877Notes

Reaction equation

HRID 919877 reaction equation
[CH3:1][NH2:2].[CH3:3][O:4][C:5](=[O:10])[CH2:6][C:7](=O)[CH3:8].[CH3:11][O:12][C:13](=[O:16])[C:14]#[CH:15]>CO>[CH3:11][O:12][C:13](=[O:16])[CH:14]=[CH:15][C:6](=[C:7]([NH:2][CH3:1])[CH3:8])[C:5]([O:4][CH3:3])=[O:10]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 7757Methyl acetoacetateHCID 13536Methyl propiolate

Product 1

HCID 86714140HCID 86714140, compoundYield 11.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
90 °C

Procedure

Methylamine (20 mL, 40 mmol, 2 M in THF) was dissolved in MeOH (130 mL). 3-Oxo-butyric acid methyl ester (5.7 mL, 48 mmol) was added, and the mixture was heated at 90° C. for 3 h in a sealed tube. After cooling the mixture to r.t., propynoic acid methyl ester (5.3 mL, 60 mmol) was added. The resulting mixture was then refluxed for 48 h. After cooling to r.t., the solvent was evaporated, and the crude residue was purified by silica gel chromatography (0-50% EtOAc/hexanes) to give 0.97 g of the title compound as a light yellow solid. 1H NMR (CDCl3, 200 MHz): δ=10.55 (br s, 1H), 7.75 (d, 1H, J=15.4 Hz), 6.06 (d, 1H, J=15.4 Hz), 3.75 (s, 3H), 3.72 (s, 3H), 3.04 (d, 3H, J=4.8 Hz), 2.26 (s, 3H).

Workup

  1. temperatureAfter cooling the mixture to r.t.
  2. temperatureThe resulting mixture was then refluxed for 48 h
  3. temperatureAfter cooling to r.t.
  4. customthe solvent was evaporated
  5. customthe crude residue was purified by silica gel chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-ab61693b237542dab5b85b447a9f9ca8
Source dataset
uspto-grants-2016_03
Patent number
US09271970B2

Reaction notes

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