Ethylmorpholine → HCID 25096711, compound

HRID 2080974Notes

Reaction equation

HRID 2080974 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:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=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:22]=[CH:21][CH:20]=[C:19]([CH3:23])[N:18]=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 131728804HCID 131728804, compound

Product 1

HCID 25096711HCID 25096711, compoundYield 61.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-methyl-1-(6-methyl-2-pyridinyl)-2-oxo-4-imidazolidinecarboxylic acid TFA salt (147 mg, 0.42 mmol), 1-hydroxybenzotriazole hydrate (96 mg, 0.63 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (121 mg, 0.63 mmol) and N-ethyl morpholine (0.27 ml, 2.1 mmol) in dichloromethane (8 ml) was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (88 mg, 0.42 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-2-pyridinyl)-2-oxo-4-imidazolidinecarboxamide (110 mg, 61%). LC/MS [M+H]+=427, retention time=2.66 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-373db5a26cac4e0a82605c1ee13dfa65
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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