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

HRID 2081013Notes

Reaction equation

HRID 2081013 reaction equation
FC(F)(F)C(O)=O.[CH3:8][N:9]1[CH:13]([C:14]([OH:16])=O)[CH2:12][N:11]([C:17]2[N:18]=[CH:19][N:20]([CH3:22])[CH:21]=2)[C:10]1=[O:23].C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:55][C:56]1[CH:61]=[C:60]([Cl:62])[CH:59]=[CH:58][C:57]=1[CH2:63][NH2:64]>ClCCl>[Cl:55][C:56]1[CH:61]=[C:60]([Cl:62])[CH:59]=[CH:58][C:57]=1[CH2:63][NH:64][C:14]([CH:13]1[CH2:12][N:11]([C:17]2[N:18]=[CH:19][N:20]([CH3:22])[CH:21]=2)[C:10](=[O:23])[N:9]1[CH3:8])=[O:16]

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 671037233-Methyl-1-(1-methyl-1h-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxylic acid trifluoroacetate salt

Product 1

HCID 25094621N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxamideYield 14.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-methyl-1-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxylic acid trifluoroacetate salt (0.105 g, 0.47 mmol) (prepared as described in step (ii) of Example 57) and N-ethyl morpholine (0.361 ml, 2.82 mmol) in dichloromethane (5 ml) was treated with 1-hydroxybenzotriazole hydrate (0.086 g, 0.564 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (0.090 g, 0.470 mmol) and stirred at room temperature for 10 minutes. 1-(2,4-Dichlorophenyl)methanamine (0.063 ml, 0.470 mmol) was added and the reaction mixture was stirred over the weekend. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine and separated using a hydrophobic frit. The filtrate was concentrated under vacuum and purified by mass-directed automated HPLC to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(1-methyl-1H-imidazol-4-yl)-2-oxo-4-imidazolidinecarboxamide (26 mg, 13.75% yield). LC/MS [M+H]+=382, retention time=1.83 minutes.

Workup

  1. stirringthe reaction mixture was stirred over the weekend
  2. washwashed with saturated sodium hydrogen carbonate solution, water and brine
  3. customseparated
  4. concentrationThe filtrate was concentrated under vacuum
  5. custompurified

Sources & evidence

ORD record
ord-348ac164227f401dbb1a5023e4d2f84b
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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