Triethylamine → 1-cyclopropyl-N-[(2,4-dichlorophenyl)methyl]-3-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxamide

HRID 546270Notes

Reaction equation

HRID 546270 reaction equation
[CH:1]1([N:4]([CH:16]([C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[O:21])[C:17](=O)[CH3:18])[C:5](=[O:15])[CH2:6]P(=O)(OCC)OCC)[CH2:3][CH2:2]1.[Cl-].[Li+].C(N(CC)CC)C>O1CCCC1>[CH:1]1([N:4]2[C:5](=[O:15])[CH:6]=[C:17]([CH3:18])[CH:16]2[C:20]([NH:22][CH2:23][C:24]2[CH:29]=[CH:28][C:27]([Cl:30])=[CH:26][C:25]=2[Cl:31])=[O:21])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 433294Lithium Chloride2×HCID 86644398Diethyl (2-{cyclopropyl[1-({[(2,4-dichlorophenyl)methyl]amino}-carbonyl)-2-oxopropyl]amino}-2-oxoethyl)phosphonate

Product 1

HCID 250296981-cyclopropyl-N-[(2,4-dichlorophenyl)methyl]-3-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxamideYield 40.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of diethyl (2-{cyclopropyl[1-({[(2,4-dichlorophenyl)methyl]amino}-carbonyl)-2-oxopropyl]amino}-2-oxoethyl)phosphonate (0.043 g, 0.087 mmol, prepared as described below) in anhydrous tetrahydrofuran (2.5 ml) at 0° C. was added lithium chloride (0.016 g, 0.39 mmol). The mixture was stirred until all of the lithium chloride dissolved and then triethylamine (0.066 ml, 0.87 mmol) was added. The mixture was allowed to warm to room temperature and stirred for 18 hrs. Evaporation of the solvent in vacuo and purification of the resulting residue by mass-directed automated HPLC gave 1-cyclopropyl-N-[(2,4-dichlorophenyl)methyl]-3-methyl-5-oxo-2,5-dihydro-1H-pyrrole-2-carboxamide (0.012 g) as a white solid.

Workup

  1. dissolutiondissolved
  2. customEvaporation of the solvent
  3. customin vacuo and purification of the resulting residue

Sources & evidence

ORD record
ord-41fe4c8aa67b4d02a57d006c0c3a4e4b
Source dataset
uspto-grants-2011_05
Patent number
US07935832B2

Reaction notes

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