Phenyl Isothiocyanate → N-[1-(3,4-Dichlorobenzyl)-piperidin-4-yl]-2-(5-phenylamino-[1,3,4]oxadiazol-2-yl)-acetamide

HRID 968273Notes

Reaction equation

HRID 968273 reaction equation
[N:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)=[C:2]=S.[Cl:10][C:11]1[CH:12]=[C:13]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:14][N:15]1[CH2:20][CH2:19][CH:18]([NH:21][C:22](=[O:28])[CH2:23][C:24]([NH:26][NH2:27])=[O:25])[CH2:17][CH2:16]1>CN(C)C=O>[Cl:10][C:11]1[CH:12]=[C:13]([CH:29]=[CH:30][C:31]=1[Cl:32])[CH2:14][N:15]1[CH2:16][CH2:17][CH:18]([NH:21][C:22](=[O:28])[CH2:23][C:24]2[O:25][C:2]([NH:1][C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=3)=[N:27][N:26]=2)[CH2:19][CH2:20]1

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 22288616N-[1-(3,4-Dichlorobenzyl)-piperidin-4-yl]-2-hydrazinocarbonyl-acetamide

Product 1

HCID 22288634N-[1-(3,4-Dichlorobenzyl)-piperidin-4-yl]-2-(5-phenylamino-[1,3,4]oxadiazol-2-yl)-acetamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Isothiocyanato-benzene (0.1 ml) and N-[1-(3,4-dichlorobenzyl)-piperidin-4-yl]-2-hydrazinocarbonyl-acetamide (0.10 g) were stirred together in dimethylformamide (2 ml) at ambient temperature for 2 hours. AM resin (0.162 g, Novabiochem, 2% DVB 1.57 mmol/g) was added and the resulting mixture was stirred at ambient temperature for 16 hours. N-cyclohexylcarbodiimide N-methyl polystyrene HL (0.319 g, Novabiochem, 1.69 mmol/g) was added and the resulting mixture was stirred at 80° C. for 24 hours, then allowed to cool. The reaction mixture was then filtered, washing with dimethylformamide (2×2 ml). The combined filtrates were evaporated and the residue was purified by reverse phase HPLC to give the title compound as a white solid. (0.045 g, m.pt 191-217° C., MS [M+H]+ (APCI+) 460/462).

Workup

  1. additionwas added
  2. stirringthe resulting mixture was stirred at 80° C. for 24 hours
  3. temperatureto cool
  4. filtrationThe reaction mixture was then filtered
  5. washwashing with dimethylformamide (2×2 ml)
  6. customThe combined filtrates were evaporated
  7. customthe residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-8acf80dc5e974e09bd225eb0a3925713
Source dataset
uspto-grants-2005_10
Patent number
US06958350B2

Reaction notes

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