1-Chloro-2-isothiocyanatobenzene → 3-[5-(2-Chloro-phenylamino)-[1,3,4]oxadiazol-2-yl]-N-[1-(3,4-dichloro-benzyl)-piperidin-4-yl]-propionamide

HRID 968269Notes

Reaction equation

HRID 968269 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]=[C:9]=S.[Cl:11][C:12]1[CH:13]=[C:14]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:15][N:16]1[CH2:21][CH2:20][CH:19]([NH:22][C:23](=[O:30])[CH2:24][CH2:25][C:26]([NH:28][NH2:29])=[O:27])[CH2:18][CH2:17]1>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]1[O:27][C:26]([CH2:25][CH2:24][C:23]([NH:22][CH:19]2[CH2:20][CH2:21][N:16]([CH2:15][C:14]3[CH:31]=[CH:32][C:33]([Cl:34])=[C:12]([Cl:11])[CH:13]=3)[CH2:17][CH2:18]2)=[O:30])=[N:28][N:29]=1

Participants

4

Reactant 2

HCID 1231711-Chloro-2-isothiocyanatobenzeneHCID 22288615HCID 22288615, compound

Product 1

HCID 98276223-[5-(2-Chloro-phenylamino)-[1,3,4]oxadiazol-2-yl]-N-[1-(3,4-dichloro-benzyl)-piperidin-4-yl]-propionamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1-Chloro-2-isothiocyanato-benzene (0.112 g) and N-[1-(3,4-dichlorobenzyl)-piperidin-4-yl]-3-hydrazinocarbonyl-propionamide (0.20 g) were stirred together in dimethylformamide (2 ml) at ambient temperature for 2 hours. AM resin (0.324 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 (0.638 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. (0.028 g, m.pt. 154-156° C., MS [M+H]+ (APCI+) 508/510).

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-8e9458f182404b00b10c1aaee895bd2a
Source dataset
uspto-grants-2005_10
Patent number
US06958350B2

Reaction notes

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