2,4-Dichlorobenzylamine → HCID 25094623, compound

HRID 2081017Notes

Reaction equation

HRID 2081017 reaction equation
[CH3:1][N:2]1[CH:6]([C:7]([OH:9])=O)[CH2:5][N:4]([C:10]2[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=2)[C:3]1=[O:16].C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:48][C:49]1[CH:54]=[C:53]([Cl:55])[CH:52]=[CH:51][C:50]=1[CH2:56][NH2:57]>ClCCl>[Cl:48][C:49]1[CH:54]=[C:53]([Cl:55])[CH:52]=[CH:51][C:50]=1[CH2:56][NH:57][C:7]([CH:6]1[CH2:5][N:4]([C:10]2[N:14]([CH3:15])[CH:13]=[N:12][CH:11]=2)[C:3](=[O:16])[N:2]1[CH3:1])=[O:9]

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 67103431HCID 67103431, compound

Product 1

HCID 25094623HCID 25094623, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-methyl-1-(1-methyl-1H-imidazol-5-yl)-2-oxo-4-imidazolidinecarboxylic acid (155 mg, 0.458 mmol) and N-ethylmorpholine (0.348 ml, 2.75 mmol) in dichloromethane (5 ml) was treated with 1-hydroxybenzotriazole hydrate (84 mg, 0.550 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (88 mg, 0.458 mmol) and stirred at room temperature for 10 minutes. 1-(2,4-Dichlorophenyl)methanamine (81 mg, 0.458 mmol) was then added and the reaction mixture was stirred at room temperature for 6 hours. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine, separated through a hydrophobic frit and the organic layer reduced under vacuum. The residue was purified by mass-directed automated HPLC to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(1-methyl-1H-imidazol-5-yl)-2-oxo-4-imidazolidinecarboxamide (63 mg, 34.2% yield). LC/MS [M+H]+=382, retention time=1.71 minutes.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 6 hours
  2. washwashed with saturated sodium hydrogen carbonate solution, water and brine
  3. customseparated through a hydrophobic frit
  4. customThe residue was purified

Sources & evidence

ORD record
ord-388e1bb036b64b4a8b09abc0ca58b4f5
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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