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 1016118Notes

Reaction equation

HRID 1016118 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-6dc654f369664d92b996facb1d28cdda
Source dataset
uspto-grants-2011_07
Patent number
US07985861B2

Reaction notes

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