Ethylmorpholine → HCID 67103243, compound

HRID 2080997Notes

Reaction equation

HRID 2080997 reaction equation
OC(C(F)(F)F)=O.[CH3:8][N:9]1[CH:13]([C:14]([OH:16])=O)[CH2:12][N:11]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:10]1=[O:25].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>[ClH:57].[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:14]([CH:13]1[CH2:12][N:11]([CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][O:22][CH2:21][CH2:20]2)[C:10](=[O:25])[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 131728810HCID 131728810, compound

Product 1

HCID 67103243HCID 67103243, compoundYield 60.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

A mixture of 3-methyl-1-[2-(4-morpholinyl)ethyl]-2-oxo-4-imidazolidinecarboxylic acid TFA salt (186 mg, 0.5 mmol), N-ethyl morpholine (0.383 ml, 3 mmol), 1-hydroxybenzotriazole hydrate (92 mg, 0.6 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (115 mg, 0.6 mmol) in dichloromethane (9 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 (1 ml) was added and the reaction stirred at room temperature for 18 hours. The mixture was diluted with dichloromethane and was washed with saturated sodium hydrogen carbonate solution. The organic phase was separated, washed with brine, dried and evaporated. The residue was purified by mass-directed automated HPLC. The product from mass-directed automated HPLC was dissolved in methanol (2 ml) and an excess of 1M hydrogen chloride in ether (0.5 ml) was added. The solvent was evaporated, the residue was triturated with ether and the solid collected and dried to give N-{[2-chloro-3-(trifluoromethyl)phenyl]methyl}-3-methyl-1-[2-(4-morpholinyl)ethyl]-2-oxo-4-imidazolidinecarboxamide hydrochloride (73 mg, 30%). LC/MS [M+H]+=449, retention time=1.80 minutes.

Workup

  1. stirringthe reaction stirred at room temperature for 18 hours
  2. washwas washed with saturated sodium hydrogen carbonate solution
  3. customThe organic phase was separated
  4. washwashed with brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified
  8. dissolutionwas dissolved in methanol (2 ml)
  9. additionan excess of 1M hydrogen chloride in ether (0.5 ml) was added
  10. customThe solvent was evaporated
  11. customthe residue was triturated with ether
  12. customthe solid collected
  13. customdried

Sources & evidence

ORD record
ord-3523760286b14911baff2a2c3ab8ad44
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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