1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 1-(4-(4-Chlorophenyl)piperidin-1-yl)-3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butan-1-one

HRID 1820188Notes

Reaction equation

HRID 1820188 reaction equation
[CH3:1][CH:2]([CH3:19])[CH:3]([NH:7][C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[N:11][N:12]=1)[C:4]([OH:6])=O.CCN=C=NCCCN(C)C.Cl.[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[CH:35][CH:34]=1.C1C=CC2N(O)N=NC=2C=1.C(N(C(C)C)CC)(C)C>CN(C=O)C.CO>[Cl:32][C:33]1[CH:38]=[CH:37][C:36]([CH:39]2[CH2:40][CH2:41][N:42]([C:4](=[O:6])[CH:3]([NH:7][C:8]3[O:9][C:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:11][N:12]=3)[CH:2]([CH3:1])[CH3:19])[CH2:43][CH2:44]2)=[CH:35][CH:34]=1

Participants

8

Reactant 5

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 27578434-(4-chlorophenyl)piperidine HydrochlorideHCID 578892573-Methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoic acid

Product 1

HCID 578889751-(4-(4-Chlorophenyl)piperidin-1-yl)-3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butan-1-oneYield 45.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

3-Methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butanoic acid (80 mg, 0.3 mmol), EDCI (65 mg, 0.33 mmol), 4-(4-chlorophenyl)-piperidine hydrochloride (78 mg, 0.33 mmol) and HOBt (40 mg, 0.3 mmol) were combined and suspended in DMF (2 mL). Diisopropylethylamine (210 μL, 1.2 mmol) was added and the reaction was stirred at rt. overnight. After this time, methanol (2 mL) was added to the reaction and the mixture was purified directly by preparative HPLC to give 1-(4-(4-chlorophenyl)piperidin-1-yl)-3-methyl-2-(5-phenyl-1,3,4-oxadiazol-2-ylamino)butan-1-one (60 mg, 30%). MS found: 439 (M+H).

Workup

  1. customovernight
  2. customthe mixture was purified directly by preparative HPLC

Sources & evidence

ORD record
ord-8f9b224b9e90412d8c068df9c8edf39a
Source dataset
uspto-grants-2009_10
Patent number
US07601844B2

Reaction notes

Loading…