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

HRID 2081063Notes

Reaction equation

HRID 2081063 reaction equation
[CH:1]1([N:6]2[CH2:10][CH:9]([C:11]([OH:13])=O)[N:8]([CH3:14])[C:7]2=[O:15])[CH2:5][CH2:4][CH2:3][CH2:2]1.C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:47][C:48]1[CH:53]=[C:52]([Cl:54])[CH:51]=[CH:50][C:49]=1[CH2:55][NH2:56]>ClCCl>[CH:1]1([N:6]2[CH2:10][CH:9]([C:11]([NH:56][CH2:55][C:49]3[CH:50]=[CH:51][C:52]([Cl:54])=[CH:53][C:48]=3[Cl:47])=[O:13])[N:8]([CH3:14])[C:7]2=[O:15])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 671036391-Cyclopentyl-3-methyl-2-oxo-4-imidazolidinecarboxylic acid

Product 1

HCID 250964681-cyclopentyl-N-[(2,4-dichlorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamideYield 62%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 1-cyclopentyl-3-methyl-2-oxo-4-imidazolidinecarboxylic acid (39 mg, 0.184 mmol), N-ethylmorpholine (0.094 ml, 0.735 mmol), 1-hydroxybenzotriazole hydrate (33.8 mg, 0.220 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (42.3 mg, 0.220 mmol) in dichloromethane (9 ml) was stirred at room temperature for 10 minutes. A solution of [1-(2,4-dichlorophenyl)methyl]amine (32.3 mg, 0.184 mmol) in dichloromethane (1 ml) was added and the reaction mixture was stirred at room temperature for 72 hours. The reaction mixture was diluted with dichloromethane (10 ml) and the mixture was washed with saturated sodium hydrogen carbonate 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 1-cyclopentyl-N-[(2,4-dichlorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (42 mg, 62%). LCMS [M+H]+=370, retention time=2.28 minutes.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 72 hours
  2. washthe mixture was washed with saturated sodium hydrogen carbonate 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-5816abfecde54e89a7b2bda04f9489f7
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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