2,4-Dichlorobenzylamine → HCID 25094896, compound

HRID 2081023Notes

Reaction equation

HRID 2081023 reaction equation
OC(C(F)(F)F)=O.[F:8][C:9]1[N:14]=[CH:13][C:12]([N:15]2[CH2:19][CH:18]([C:20]([OH:22])=O)[N:17]([CH3:23])[C:16]2=[O:24])=[CH:11][CH:10]=1.C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)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:20]([CH:18]1[CH2:19][N:15]([C:12]2[CH:13]=[N:14][C:9]([F:8])=[CH:10][CH:11]=2)[C:16](=[O:24])[N:17]1[CH3:23])=[O:22]

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 131728814HCID 131728814, compound

Product 1

HCID 25094896HCID 25094896, compoundYield 18.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(6-fluoro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid TFA salt (200 mg, 0.836 mmol) and N-ethylmorpholine (0.635 ml, 5.02 mmol) in dichloromethane (10 ml) was added 1-hydroxybenzotriazole hydrate (128 mg, 0.836 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (160 mg, 0.836 mmol) and the mixture was stirred for 10 minutes. 1-(2,4-Dichlorophenyl)methanamine (147 mg, 0.836 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and 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 FFlashmaster automated silica gel chromatography eluting with 10-100% ethyl acetate in isohexane to give N-[(2,4-dichlorophenyl)methyl]-1-(6-fluoro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide (60 mg, 18% yield). LC/MS [M+H]+=397, retention time=2.63 minutes.

Workup

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

Sources & evidence

ORD record
ord-f5372f9823f04e0e8657c78df89a76d3
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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