Ethylmorpholine → N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,6-dimethyl-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide

HRID 2081007Notes

Reaction equation

HRID 2081007 reaction equation
OC(C(F)(F)F)=O.[CH3:8][C:9]1[C:14]([N:15]2[CH2:19][CH:18]([C:20]([OH:22])=O)[N:17]([CH3:23])[C:16]2=[O:24])=[CH:13][CH:12]=[C:11]([CH3:25])[N:10]=1.C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:57][C:58]1[C:63]([C:64]([F:67])([F:66])[F:65])=[CH:62][CH:61]=[CH:60][C:59]=1[CH2:68][NH2:69]>ClCCl>[Cl:57][C:58]1[C:63]([C:64]([F:66])([F:67])[F:65])=[CH:62][CH:61]=[CH:60][C:59]=1[CH2:68][NH:69][C:20]([CH:18]1[CH2:19][N:15]([C:14]2[C:9]([CH3:8])=[N:10][C:11]([CH3:25])=[CH:12][CH:13]=2)[C:16](=[O:24])[N:17]1[CH3:23])=[O:22]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 52242072-Chloro-3-(trifluoromethyl)benzylamineHCID 1317288121-(2,6-dimethyl-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid TFA salt

Product 1

HCID 25094618N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,6-dimethyl-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamideYield 47.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of crude 1-(2,6-dimethyl-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid TFA salt (10 ml of 0.05M solution in DCM, 0.5 mmol), N-ethylmorpholine (0.383 ml, 3.00 mmol), 1-hydroxybenzotriazole hydrate (92 mg, 0.600 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (115 mg, 0.600 mmol) was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (105 mg, 0.5 mmol) in dichloromethane (1 ml) was added and the reaction stirred at room temperature for 18 hours. The reaction mixture was diluted with dichloromethane and the solution was washed with saturated sodium hydrogen carbonate solution, water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 0-10% methanol in dichloromethane. The residue was triturated with ether and the resulting solid was collected and dried to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-(2,6-dimethyl-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide (104 mg, 47%). LC/MS [M+H]+=441, retention time=1.86 minutes.

Workup

  1. stirringthe reaction stirred at room temperature for 18 hours
  2. washthe solution was washed with saturated sodium hydrogen carbonate solution, water and brine
  3. customdried
  4. customevaporated
  5. customThe residue was purified by silica gel chromatography
  6. washeluting with 0-10% methanol in dichloromethane
  7. customThe residue was triturated with ether
  8. customthe resulting solid was collected
  9. customdried

Sources & evidence

ORD record
ord-410bd239da124bde8e3e32540d2fbf8f
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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