Dimethyl Sulfoxide → N-[(1-carbamimidoylpiperidin-4-yl)methyl]-3-[2-(2,4-dichlorophenyl)ethoxy]-4-methoxybenzamide

HRID 2114810Notes

Reaction equation

HRID 2114810 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH2:10][O:11][C:12]1[CH:13]=[C:14]([CH:18]=[CH:19][C:20]=1[O:21][CH3:22])[C:15]([OH:17])=O.C(N1C=CN=C1)(N1C=CN=C1)=O.Cl.[NH2:36][CH2:37][CH:38]1[CH2:43][CH2:42][N:41]([C:44]([NH2:46])=[NH:45])[CH2:40][CH2:39]1.CS(C)=O>CN(C=O)C>[C:44]([N:41]1[CH2:42][CH2:43][CH:38]([CH2:37][NH:36][C:15](=[O:17])[C:14]2[CH:18]=[CH:19][C:20]([O:21][CH3:22])=[C:12]([O:11][CH2:10][CH2:9][C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[CH:13]=2)[CH2:39][CH2:40]1)(=[NH:45])[NH2:46]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 682631,1'-CarbonyldiimidazoleHCID 154803323-[2-(2,4-Dichlorophenyl)ethoxy]-4-methoxybenzoic acidHCID 177949434-Aminomethyl-piperidine-1-carboxamidine hydrochloride

Product 1

HCID 10162765N-[(1-carbamimidoylpiperidin-4-yl)methyl]-3-[2-(2,4-dichlorophenyl)ethoxy]-4-methoxybenzamideYield 21.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 100 mg 3-[2-(2,4-Dichlorophenyl)-ethoxy]-4-methoxy-benzoic acid in 2 ml DMF was activated by the addition of 53 mg carbonyldiimidazole. After stirring for 2 h at RT 90 mg of 4-Aminomethyl-piperidine-1-carboxamidine hydrochloride and 2 ml DMSO were added and the mixture was stirred overnight. Subsequent dilution with 3 ml water and filtration through a chem elut® cartridge, eluting with ethyl acetate yielded after concentration under reduced pressure a white solid. Purification by preparative HPLC (C18 reverse phase column, elution with a H2O/MeCN gradient with 0.5% TFA) and lyophilisation afforded 30 mg (20%) of the title compound as a white powder.

Workup

  1. additionwere added
  2. filtrationSubsequent dilution with 3 ml water and filtration through a chem elut® cartridge
  3. washeluting with ethyl acetate
  4. customyielded
  5. concentrationafter concentration under reduced pressure a white solid
  6. customPurification by preparative HPLC (
  7. washC18 reverse phase column, elution with a H2O/MeCN gradient with 0.5% TFA) and lyophilisation

Sources & evidence

ORD record
ord-343486162e4f459a8379f6a34dbc91d1
Source dataset
uspto-grants-2008_10
Patent number
US07435747B2

Reaction notes

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