2,4-Dichlorobenzylamine → HCID 25095177, compound

HRID 2081040Notes

Reaction equation

HRID 2081040 reaction equation
[Cl:1][C:2]1[C:7]([N:8]2[CH2:12][CH:11]([C:13]([OH:15])=O)[N:10]([CH3:16])[C:9]2=[O:17])=[CH:6][CH:5]=[CH:4][N:3]=1.C(N1CCOCC1)C.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.[Cl:49][C:50]1[CH:55]=[C:54]([Cl:56])[CH:53]=[CH:52][C:51]=1[CH2:57][NH2:58]>ClCCl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:12][CH:11]([C:13]([NH:58][CH2:57][C:51]3[CH:52]=[CH:53][C:54]([Cl:56])=[CH:55][C:50]=3[Cl:49])=[O:15])[N:10]([CH3:16])[C:9]2=[O:17])=[CH:6][CH:5]=[CH:4][N:3]=1

Participants

7

Reactant 5

HCID 14852,4-DichlorobenzylamineHCID 7525EthylmorpholineHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27960291-Hydroxybenzotriazole hydrateHCID 86640214HCID 86640214, compound

Product 1

HCID 25095177HCID 25095177, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(2-chloro-3-pyridinyl)-3-methyl-2-oxo-4-imidazolidinecarboxylic acid (179 mg, 0.484 mmol) and N-ethylmorpholine (0.368 ml, 2.91 mmol) in dichloromethane (5 ml) was added 1-hydroxybenzotriazole hydrate (111 mg, 0.726 mmol) and 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (139 mg, 0.726 mmol) and the mixture was stirred for 10 minutes at room temperature. 1-(2,4-Dichlorophenyl)methanamine (128 mg, 0.726 mmol) was added and the reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with dichloromethane and washed with saturated sodium hydrogen carbonate solution, water and brine and separated by hydrophobic frit and the solution was reduced under vacuum. The residue was purified by SP4 automated silica gel chromatography eluting with 10-100% ethyl acetate in isohexane to give 1-(2-chloro-3-pyridinyl)-N-[(2,4-dichlorophenyl)methyl]-3-methyl-2-oxo-4-imidazolidinecarboxamide (60 mg, 27.6% yield). LC/MS [M+H]+=413, retention time=2.21 minutes

Workup

  1. stirringthe reaction mixture was stirred at room temperature overnight
  2. washwashed with saturated sodium hydrogen carbonate solution, water and brine
  3. customseparated by 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-53d62da84d3c426ba18a6ae347568da5
Source dataset
uspto-grants-2011_04
Patent number
US07932282B2

Reaction notes

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