Ethylmorpholine → HCID 59252117, compound

HRID 2081002Notes

Reaction equation

HRID 2081002 reaction equation
[CH3:1][N:2]1[CH2:6][CH:5]([C:7]([OH:9])=O)[NH:4][C:3]1=[O:10].C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:42][C:43]1[C:48]([C:49]([F:52])([F:51])[F:50])=[CH:47][CH:46]=[CH:45][C:44]=1[CH2:53][NH2:54]>ClCCl>[Cl:42][C:43]1[C:48]([C:49]([F:51])([F:52])[F:50])=[CH:47][CH:46]=[CH:45][C:44]=1[CH2:53][NH:54][C:7]([CH:5]1[CH2:6][N:2]([CH3:1])[C:3](=[O:10])[NH:4]1)=[O:9]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 52242072-Chloro-3-(trifluoromethyl)benzylamineHCID 138529991-Methyl-2-oxoimidazolidine-4-carboxylic acid

Product 1

HCID 59252117HCID 59252117, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 1-methyl-2-oxo-4-imidazolidinecarboxylic acid (144 mg, 1 mmol), N-ethyl morpholine (0.767 ml, 6.00 mmol), 1-hydroxybenzotriazole hydrate (184 mg, 1.200 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (230 mg, 1.200 mmol) in dichloromethane (18 ml) was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (210 mg, 1.000 mmol) in dichloromethane (2 ml) was added and the reaction stirred at room temperature for hours. The mixture was diluted with dichloromethane and the mixture was washed with 3N citric acid solution. The organic phase was separated, washed with brine, dried and evaporated. The residue was purified by mass-directed automated HPLC to give the N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-1-methyl-2-oxo-4-imidazolidinecarboxamide (150 mg, 55%). LC/MS [M+H]+=336, retention time=2.22 minutes.

Workup

  1. stirringthe reaction stirred at room temperature for hours
  2. washthe mixture was washed with 3N citric acid solution
  3. customThe organic phase was separated
  4. washwashed with brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-c39e31b1de224a428f9837d4eff9715b
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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