Ethylmorpholine → HCID 25098010, compound

HRID 2080972Notes

Reaction equation

HRID 2080972 reaction equation
OC(C(F)(F)F)=O.[CH3:8][N:9]1[CH:13]([C:14]([OH:16])=O)[CH2:12][N:11]([C:17]2[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[C:10]1=[O:24].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N1CCOCC1)C.[Cl:56][C:57]1[C:62]([C:63]([F:66])([F:65])[F:64])=[CH:61][CH:60]=[CH:59][C:58]=1[CH2:67][NH2:68]>ClCCl>[Cl:56][C:57]1[C:62]([C:63]([F:65])([F:66])[F:64])=[CH:61][CH:60]=[CH:59][C:58]=1[CH2:67][NH:68][C:14]([CH:13]1[CH2:12][N:11]([C:17]2[CH:18]=[N:19][C:20]([CH3:23])=[CH:21][CH:22]=2)[C:10](=[O:24])[N:9]1[CH3:8])=[O:16]

Participants

7

Reactant 5

HCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 52242072-Chloro-3-(trifluoromethyl)benzylamineHCID 131728803HCID 131728803, compound

Product 1

HCID 25098010HCID 25098010, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-methyl-1-(6-methyl-3-pyridinyl)-2-oxo-4-imidazolidinecarboxylic acid TFA salt (175 mg, 0.5 mmol), 1-hydroxybenzotriazole hydrate (115 mg, 0.75 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (144 mg, 0.75 mmol) and N-ethyl morpholine (0.319 ml, 2.5 mmol) in dichloromethane (8 ml) 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 (2 ml) was added and the reaction stirred at room temperature for 4 hours. The mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate solution. The organic phase was separated, washed with water and brine, dried and evaporated. The residue was purified by silica gel chromatography eluting with 0-10% methanol in dichloromethane to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-(6-methyl-3-pyridinyl)-2-oxo-4-imidazolidinecarboxamide (95 mg, 44%). LC/MS [M+H]+=427, retention time=1.98 minutes.

Workup

  1. stirringthe reaction stirred at room temperature for 4 hours
  2. customThe mixture was partitioned between dichloromethane and saturated sodium hydrogen carbonate solution
  3. customThe organic phase was separated
  4. washwashed with water and brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified by silica gel chromatography
  8. washeluting with 0-10% methanol in dichloromethane

Sources & evidence

ORD record
ord-53edd033c6104bd0a63390919a059d28
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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