Ethylmorpholine → N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1-(3-methyl-2-pyridinyl)-2-oxo-4-imidazolidinecarboxamide

HRID 2080983Notes

Reaction equation

HRID 2080983 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[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][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.[Cl:57][C:58]1[C:63]([F:64])=[C:62]([F:65])[CH:61]=[CH:60][C:59]=1[CH2:66][NH2:67]>ClCCl>[Cl:57][C:58]1[C:63]([F:64])=[C:62]([F:65])[CH:61]=[CH:60][C:59]=1[CH2:66][NH:67][C:14]([CH:13]1[CH2:12][N:11]([C:17]2[C:22]([CH3:23])=[CH:21][CH:20]=[CH:19][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 67103566(2-Chloro-3,4-difluorophenyl)methanamine hydrochlorideHCID 1317288073-methyl-1-(3-methyl-2-pyridinyl)-2-oxo-4-imidazolidinecarboxylic acid TFA salt

Product 1

HCID 25098015N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1-(3-methyl-2-pyridinyl)-2-oxo-4-imidazolidinecarboxamideYield 46%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-methyl-1-(3-methyl-2-pyridinyl)-2-oxo-4-imidazolidinecarboxylic acid TFA salt (279 mg, 0.8 mmol), 1-hydroxybenzotriazole hydrate (147 mg, 0.96 mmol), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (184 mg, 0.96 mmol) and N-ethyl morpholine (0.613 ml, 4.8 mmol) in dichloromethane (20 ml) was stirred at room temperature for 10 minutes. [(2-Chloro-3,4-difluorophenyl)methyl]amine hydrochloride (171 mg, 0.8 mmol) was added and the reaction stirred at room temperature for 18 hours. The mixture was diluted with dichloromethane and was washed with 3N citric acid solution. The organic phase was separated, washed with brine, dried and evaporated. The residue was purified by mass-directed automated HPLC to give N-[(2-chloro-3,4-difluorophenyl)methyl]-3-methyl-1-(3-methyl-2-pyridinyl)-2-oxo-4-imidazolidinecarboxamide (145 mg, 46%). LC/MS [M+H]+=395, retention time=2.36 minutes.

Workup

  1. stirringthe reaction stirred at room temperature for 18 hours
  2. washwas washed with 3N citric acid solution
  3. customThe organic phase was separated
  4. washwashed with brine
  5. customdried
  6. customevaporated
  7. customThe residue was purified

Sources & evidence

ORD record
ord-2df7f241e3784d23a278fbaeb83b0c0d
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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