Ethylmorpholine → HCID 25094622, compound

HRID 2081014Notes

Reaction equation

HRID 2081014 reaction equation
[CH3:1][N:2]1[CH:6]([C:7]([OH:9])=O)[CH2:5][N:4]([C:10]2[N:11]([CH3:15])[CH:12]=[CH:13][N:14]=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[C:54]([C:55]([F:58])([F:57])[F:56])=[CH:53][CH:52]=[CH:51][C:50]=1[CH2:59][NH2:60]>ClCCl>[Cl:48][C:49]1[C:54]([C:55]([F:57])([F:58])[F:56])=[CH:53][CH:52]=[CH:51][C:50]=1[CH2:59][NH:60][C:7]([CH:6]1[CH2:5][N:4]([C:10]2[N:11]([CH3:15])[CH:12]=[CH:13][N:14]=2)[C:3](=[O:16])[N:2]1[CH3:1])=[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 671034053-methyl-1-(1-methyl-1H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid

Product 1

HCID 25094622HCID 25094622, compoundYield 31.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 3-methyl-1-(1-methyl-1H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxylic acid (166 mg, 0.517 mmol) and N-ethyl morpholine (0.397 ml, 3.10 mmol) in dichloromethane (5 ml) was treated with 1-hydroxybenzotriazole hydrate (95 mg, 0.620 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (99 mg, 0.517 mmol) and stirred at room temperature for 10 minutes. 1-[2-Chloro-3-(trifluoromethyl)phenyl]methanamine (108 mg, 0.517 mmol) was then added and the reaction stirred overnight at room temperature. 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 was reduced under vacuum. The residue was purified by mass-directed automated HPLC to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(1-methyl-1H-imidazol-2-yl)-2-oxo-4-imidazolidinecarboxamide (67 mg, 29.6% yield). LC/MS [M+H]+=416, retention time=1.89 minutes.

Workup

  1. stirringthe reaction stirred overnight at room temperature
  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-2890629326584f5f8492786531889469
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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