2,4-Dichlorobenzylamine → N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(2-methyl-3-pyridinyl)-2-oxo-4-imidazolidinecarboxamide

HRID 2080977Notes

Reaction equation

HRID 2080977 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:18]([CH3:23])=[N:19][CH:20]=[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[CH:62]=[C:61]([Cl:63])[CH:60]=[CH:59][C:58]=1[CH2:64][NH2:65]>ClCCl>[Cl:56][C:57]1[CH:62]=[C:61]([Cl:63])[CH:60]=[CH:59][C:58]=1[CH2:64][NH:65][C:14]([CH:13]1[CH2:12][N:11]([C:17]2[C:18]([CH3:23])=[N:19][CH:20]=[CH:21][CH:22]=2)[C:10](=[O:24])[N:9]1[CH3:8])=[O:16]

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 1317288053-methyl-1-(2-methyl-3-pyridinyl)-2-oxo-4-imidazolidinecarboxylic acid TFA salt

Product 1

HCID 25098012N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(2-methyl-3-pyridinyl)-2-oxo-4-imidazolidinecarboxamideYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 3-methyl-1-(2-methyl-3-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 (18 ml) was stirred at room temperature for 10 minutes. A solution of [1-(2,4-dichlorophenyl)methyl]amine (141 mg, 0.8 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-[(2,4-dichlorophenyl)methyl]-3-methyl-1-(2-methyl-3-pyridinyl)-2-oxo-4-imidazolidinecarboxamide (147 mg, 47%). LC/MS [M+H]+=393, retention time=1.76 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-9fce2e52aed04557872d44c31fc597c2
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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