2,4-Dichlorobenzylamine → N-[(2,4-dichlorophenyl)methyl]-1-(5-fluoro-2-pyrimidinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide

HRID 2081045Notes

Reaction equation

HRID 2081045 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([N:8]2[CH2:12][CH:11]([C:13]([OH:15])=O)[N:10]([CH3:16])[C:9]2=[O:17])=[N:6][CH:7]=1.C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:49][C:50]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:51]=1[CH2:57][NH2:58]>ClCCl.C(OCC)C>[Cl:49][C:50]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:51]=1[CH2:57][NH:58][C:13]([CH:11]1[CH2:12][N:8]([C:5]2[N:6]=[CH:7][C:2]([F:1])=[CH:3][N:4]=2)[C:9](=[O:17])[N:10]1[CH3:16])=[O:15]

Participants

8

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 671036301-(5-Fluoro-2-pyrimidinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid

Product 1

HCID 25095444N-[(2,4-dichlorophenyl)methyl]-1-(5-fluoro-2-pyrimidinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamideYield 53.5%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Procedure

1-(5-Fluoro-2-pyrimidinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid (211 mg, 0.878 mmol) was suspended in dichloromethane (5 ml) under argon and treated with N-ethylmorpholine (0.667 ml, 5.27 mmol), 1-hydroxybenzotriazole hydrate (161 mg, 1.054 mmol), and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (202 mg, 1.054 mmol) and stirred at room temperature for ˜5 minutes. The mixture was then treated with 1-(2,4-dichlorophenyl)methanamine (0.117 ml, 0.878 mmol) and left to stir overnight at room temperature. The mixture was diluted with dichloromethane (˜10 ml) and washed with saturated sodium hydrogen carbonate solution, water, 10% aqueous citric acid, water, and brine, then filtered through a hydrophobic frit and evaporated. Trituration of the resulting oil with diethyl ether gave N-[(2,4-dichlorophenyl)methyl]-1-(5-fluoro-2-pyrimidinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide (187 mg, 53.5% yield) as a white solid which was collected by filtration and dried in vacuo. LC/MS [M+H]+=398, retention time=2.12 minutes.

Workup

  1. waitleft
  2. stirringto stir overnight at room temperature
  3. washwashed with saturated sodium hydrogen carbonate solution, water, 10% aqueous citric acid, water, and brine
  4. filtrationfiltered through a hydrophobic frit
  5. customevaporated

Sources & evidence

ORD record
ord-77ef512fda584ecd94d98d4b633dff65
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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