2,4-Dichlorobenzylamine → N-[(2,4-dichlorophenyl)methyl]-1-methyl-2-oxo-3-(2,2,2-trifluoroethyl)-4-imidazolidinecarboxamide

HRID 2081032Notes

Reaction equation

HRID 2081032 reaction equation
[CH3:1][N:2]1[CH2:6][CH:5]([C:7]([OH:9])=O)[N:4]([CH2:10][C:11]([F:14])([F:13])[F:12])[C:3]1=[O:15].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N1CCOCC1)C.[Cl:47][C:48]1[CH:53]=[C:52]([Cl:54])[CH:51]=[CH:50][C:49]=1[CH2:55][NH2:56]>ClCCl>[Cl:47][C:48]1[CH:53]=[C:52]([Cl:54])[CH:51]=[CH:50][C:49]=1[CH2:55][NH:56][C:7]([CH:5]1[CH2:6][N:2]([CH3:1])[C:3](=[O:15])[N:4]1[CH2:10][C:11]([F:14])([F:13])[F:12])=[O:9]

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 671036651-Methyl-2-oxo-3-(2,2,2-trifluoroethyl)-4-imidazolidinecarboxylic acid

Product 1

HCID 25094901N-[(2,4-dichlorophenyl)methyl]-1-methyl-2-oxo-3-(2,2,2-trifluoroethyl)-4-imidazolidinecarboxamideYield 42.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 1-methyl-2-oxo-3-(2,2,2-trifluoroethyl)-4-imidazolidinecarboxylic acid (84 mg, 0.37 mmol), 1-hydroxybenzotriazole hydrate (68.0 mg, 0.444 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (85 mg, 0.444 mmol) and N-ethyl morpholine (0.189 ml, 1.480 mmol) in dichloromethane (9 ml) was stirred at room temperature for 10 minutes. A solution of [1-(2,4-dichlorophenyl)methyl]amine (65.1 mg, 0.37 mmol) in dichloromethane (1 ml) was added and the reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane (10 ml) and the solution was washed with saturated sodium hydrogen carbonate solution (10 ml), water (10 ml), citric acid solution (10 ml) and brine (10 ml), dried and evaporated. The residue was purified by mass-directed automated HPLC. The residue was triturated with ether and the resulting solid was collected and dried to give N-[(2,4-dichlorophenyl)methyl]-1-methyl-2-oxo-3-(2,2,2-trifluoroethyl)-4-imidazolidinecarboxamide (60 mg, 42%). LC/MS [M+H]+=384, retention time=2.64 minutes.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 18 hours
  2. washthe solution was washed with saturated sodium hydrogen carbonate solution (10 ml), water (10 ml), citric acid solution (10 ml) and brine (10 ml)
  3. customdried
  4. customevaporated
  5. customThe residue was purified
  6. customThe residue was triturated with ether
  7. customthe resulting solid was collected
  8. customdried

Sources & evidence

ORD record
ord-412213eafe8c4b6eb6ab23432581b3d7
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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