Sodium Bicarbonate → N-(2,4-dimethoxybenzyl)-N-prop-2-yn-1-yl-1H-pyrrole-2-carboxamide

HRID 1172786Notes

Reaction equation

HRID 1172786 reaction equation
[NH:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]([O:8]N1C(=O)CCC1=O)=O.[CH3:16][O:17][C:18]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:19]=1[CH2:20][NH:21][CH2:22][C:23]#[CH:24].C([O-])(O)=O.[Na+]>CC#N.O>[CH3:16][O:17][C:18]1[CH:28]=[C:27]([O:29][CH3:30])[CH:26]=[CH:25][C:19]=1[CH2:20][N:21]([CH2:22][C:23]#[CH:24])[C:6]([C:2]1[NH:1][CH:5]=[CH:4][CH:3]=1)=[O:8]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 64216601-[(1H-Pyrrol-2-ylcarbonyl)oxy]-2,5-pyrrolidinedioneHCID 28419238N-(2,4-dimethoxybenzyl)prop-2-yn-1-amine

Product 1

HCID 86633422N-(2,4-dimethoxybenzyl)-N-prop-2-yn-1-yl-1H-pyrrole-2-carboxamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

A solution of 1-[(1H-pyrrol-2-ylcarbonyl)oxy]pyrrolidine-2,5-dione (1 eq), N-(2,4-dimethoxybenzyl)prop-2-yn-1-amine (1.05 eq) and NaHCO3 (1 eq) in a mixture of CH3CN and H2O (20:1) was heated at reflux for 12 hrs and then the MeCN was removed under reduced pressure. The resulting residue was partitioned between DCM and sat. aq. NaHCO3 solution. The organic phase was dried (Na2SO4), filtered, concentrated under reduced pressure and the resulting brown oil was purified by Biotage system eluting with EtOAc/petrol ether to obtain the desired amide. MS (ES) C17H18N2O3 requires: 298, found: 299 (M+H)+. 1H NMR (300 MHz, DMSO-d6) δ: 11.56 (1H, br. S), 7.40 (1H, d, J=8.3 Hz), 6.91 (1H, s), 6.60 (1H, d, J=2.1 Hz), 6.52 (1H, dd, J=8.3, 2.1 Hz), 6.48-6.35 (1H, m), 6.09 (1H, s), 4.68 (2H, s), 4.22 (2H, s), 3.80 (3H, s), 3.76 (3H, s), 3.24 (1H, s).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 12 hrs
  3. customthe MeCN was removed under reduced pressure
  4. customThe resulting residue was partitioned between DCM and sat. aq. NaHCO3 solution
  5. dry with materialThe organic phase was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customthe resulting brown oil was purified by Biotage system
  9. washeluting with EtOAc/petrol ether

Sources & evidence

ORD record
ord-097b6373631244b790c3d744c4039a1f
Source dataset
uspto-grants-2010_11
Patent number
US07834015B2

Reaction notes

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