Ethylmorpholine → HCID 25098014, compound

HRID 2080980Notes

Reaction equation

HRID 2080980 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]=[CH:19][N:18]=2)[C:10]1=[O:23].O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(N1CCOCC1)C.[Cl:55][C:56]1[C:61]([C:62]([F:65])([F:64])[F:63])=[CH:60][CH:59]=[CH:58][C:57]=1[CH2:66][NH2:67]>ClCCl>[Cl:55][C:56]1[C:61]([C:62]([F:64])([F:65])[F:63])=[CH:60][CH:59]=[CH:58][C:57]=1[CH2:66][NH:67][C:14]([CH:13]1[CH2:12][N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][N:18]=2)[C:10](=[O:23])[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 131728806HCID 131728806, compound

Product 1

HCID 25098014HCID 25098014, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-methyl-2-oxo-1-(2-pyridinyl)-4-imidazolidinecarboxylic acid TFA salt (117 mg, 0.35 mmol), 1-hydroxybenzotriazole hydrate (80 mg, 0.525 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (101 mg, 0.525 mmol) and N-ethyl morpholine (0.224 ml, 1.75 mmol) in dichloromethane (8 ml) was stirred at room temperature for 10 minutes. A solution of {[2-chloro-3-(trifluoromethyl)phenyl]methyl}amine (73.4 mg, 0.35 mmol) in dichloromethane (2 ml) was added and the reaction stirred at room temperature for 18 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-2-oxo-1-(2-pyridinyl)-4-imidazolidinecarboxamide (90 mg, 62%). LC/MS [M+H]+=413, retention time=2.55 minutes.

Workup

  1. stirringthe reaction stirred at room temperature for 18 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-bdb9384a79954d68bc550de425402996
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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