1,1'-Carbonyldiimidazole → N-(1-benzyl-4-piperidinyl)-3-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]propanamide

HRID 1070514Notes

Reaction equation

HRID 1070514 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([CH2:12][CH2:13][C:14]([OH:16])=O)[O:9][N:8]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39]([NH2:42])[CH2:38][CH2:37]1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>O1CCCC1>[CH2:29]([N:36]1[CH2:41][CH2:40][CH:39]([NH:42][C:14](=[O:16])[CH2:13][CH2:12][C:10]2[O:9][N:8]=[C:7]([C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=3)[N:11]=2)[CH2:38][CH2:37]1)[C:30]1[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 4158521-Benzyl-4-piperidylamineHCID 31643283-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)propanoic acid

Product 1

HCID 22396254N-(1-benzyl-4-piperidinyl)-3-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]propanamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 3-(3-Pyridin-2-yl-[1,2,4]oxadiazol-5-yl)-propionic acid (1 g) in tetrahydrofuran (5 ml), was added carbonyldiimidazole (0.74 g). The mixture was stirred for 10 minutes before addition of 1-benzyl-piperidin-4-ylamine (1 ml) in tetrahydrofuran (5 ml). The reaction mixture was stirred for 15 minutes then partitioned between ethyl acetate (20 ml) and water (20 ml). The organic layer was separated, dried (MgSO4) and solvent removed by evaporation. Purification by Biotage® 40S eluting 3%MeOH/0.5% 880 ammonia/dichloromethane gave the title compound (0.93 g).

Workup

  1. customthen partitioned between ethyl acetate (20 ml) and water (20 ml)
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4) and solvent
  4. customremoved by evaporation
  5. customPurification by Biotage® 40S
  6. washeluting 3%MeOH/0.5% 880 ammonia/dichloromethane

Sources & evidence

ORD record
ord-f5f45242cfe04f309673b9a602830a65
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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