2,4-Dichlorobenzylamine → HCID 25094898, compound

HRID 2081026Notes

Reaction equation

HRID 2081026 reaction equation
OC(C(F)(F)F)=O.[F:8][C:9]1[C:14]([N:15]2[CH2:19][CH:18]([C:20]([OH:22])=O)[N:17]([CH3:23])[C:16]2=[O:24])=[CH:13][CH:12]=[CH:11][N: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:14]2[C:9]([F:8])=[N:10][CH:11]=[CH:12][CH:13]=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 131728815HCID 131728815, compound

Product 1

HCID 25094898HCID 25094898, compoundYield 41.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(2-fluoro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid TFA salt (182 mg, 0.761 mmol) and N-ethylmorpholine (0.578 ml, 4.57 mmol) in dichloromethane (5 ml) was added 1-hydroxybenzotriazole hydrate (117 mg, 0.761 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (146 mg, 0.761 mmol) and the reaction mixture was stirred for 10 minutes at room temperature. 1-(2,4-Dichlorophenyl)methanamine (134 mg, 0.761 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]-1-(2-fluoro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxamide (125 mg, 40.5% yield)

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-a2dac6f5ba944a018cbbb7194dfe7c28
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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