Methylamine → HCID 86714140, compound

HRID 1410883Notes

Reaction equation

HRID 1410883 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-4cef363a2c204dd78807a49939e5b9f5
Source dataset
uspto-grants-2014_12
Patent number
US08921389B2

Reaction notes

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