2,4-Dichlorobenzylamine → n-[(2,4-Dichlorophenyl)methyl]-3-methyl-1-[6-(methyloxy)-3-pyridinyl]-2-oxo-4-imidazolidinecarboxamide

HRID 2081029Notes

Reaction equation

HRID 2081029 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:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=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[CH:63]=[C:62]([Cl:64])[CH:61]=[CH:60][C:59]=1[CH2:65][NH2:66]>ClCCl>[Cl:57][C:58]1[CH:63]=[C:62]([Cl:64])[CH:61]=[CH:60][C:59]=1[CH2:65][NH:66][C:14]([CH:13]1[CH2:12][N:11]([C:17]2[CH:18]=[N:19][C:20]([O:23][CH3:24])=[CH:21][CH:22]=2)[C:10](=[O:25])[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 1317288163-methyl-1-[6-(methyloxy)-3-pyridinyl]-2-oxo-4-imidazolidinecarboxylic acid TFA salt

Product 1

HCID 25094900n-[(2,4-Dichlorophenyl)methyl]-3-methyl-1-[6-(methyloxy)-3-pyridinyl]-2-oxo-4-imidazolidinecarboxamideYield 61.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-methyl-1-[6-(methyloxy)-3-pyridinyl]-2-oxo-4-imidazolidinecarboxylic acid TFA salt (145 mg, 0.404 mmol) and N-ethylmorpholine (0.307 ml, 2.424 mmol) in dichloromethane (5 ml) was added 1-hydroxybenzotriazole hydrate (61.9 mg, 0.404 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (77 mg, 0.404 mmol) and the reaction mixture was stirred for 10 minutes at room temperature. 1-(2,4-Dichlorophenyl)methanamine (71.1 mg, 0.404 mmol) was added and the reaction was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and the solution was washed with saturated sodium hydrogen carbonate solution, water and brine, separated through a hydrophobic frit and the organic layer was reduced under vacuum. The residue was purified by SP4 automated silica gel chromatography eluting with 10-100% ethyl acetate in isohexane to give N-[(2,4-dichlorophenyl)methyl]-3-methyl-1-[6-(methyloxy)-3-pyridinyl]-2-oxo-4-imidazolidinecarboxamide (101 mg, 59.9% yield). LC/MS [M+H]+=409, retention time=2.34 minutes.

Workup

  1. stirringthe reaction was stirred at room temperature overnight
  2. washthe solution was washed with saturated sodium hydrogen carbonate solution, water and brine
  3. customseparated through a hydrophobic frit
  4. customThe residue was purified by SP4 automated silica gel chromatography
  5. washeluting with 10-100% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-99fbd6a4a9a94e59b6a63f71b1c3b1ee
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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