Triethylamine → Cis-N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxamide

HRID 1070503Notes

Reaction equation

HRID 1070503 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[N:11]=[C:10]([C@H:12]2[CH2:14][C@H:13]2[C:15]([OH:17])=O)[O:9][N:8]=1.Cl.[Cl:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:23][N:24]1[CH2:29][CH2:28][CH:27]([NH2:30])[CH2:26][CH2:25]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>ClCCl>[Cl:19][C:20]1[CH:21]=[C:22]([CH:31]=[CH:32][C:33]=1[Cl:34])[CH2:23][N:24]1[CH2:25][CH2:26][CH:27]([NH:30][C:15]([C@@H:13]2[CH2:14][C@@H:12]2[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)=[O:17])[CH2:28][CH2:29]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 12018241cis-2-[3-(2-Pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxylic acidHCID 223962061-(3,4-Dichloro-benzyl)-piperidin-4-ylamine hydrochloride

Product 1

HCID 68886716Cis-N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxamideYield 19%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Cis-2-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxylic acid (0.139 g) and N,N′-carbonyldiimidazole (0.110 g) in dichloromethane was stirred under nitrogen for 1 hour. 1-(3,4-dichlorobenzyl)-4-piperidinamine hydrochloride (0.198 g), and triethylamine (0.121 g) was then added and allowed to stir for 24 hours under nitrogen. Saturated sodium hydrogen carbonate was added to the reaction with the resulting solution being extracted three times with dichloromethane. The pooled organic phases were washed once with water, once with brine, dried over magnesium sulfate, filtered and the solvent removed under reduced pressure to leave an oil. This oil was purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile). The solvent was removed under reduced pressure to leave Cis-N-[1-(3,4-dichlorobenzyl)-4-piperidinyl]-2-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]cyclopropanecarboxamide (0.054 g) as a white solid.

Workup

  1. extractionbeing extracted three times with dichloromethane
  2. washThe pooled organic phases were washed once with water, once with brine
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customthe solvent removed under reduced pressure
  6. customto leave an oil
  7. customThis oil was purified by RPHPLC (75%-5%, 0.1% ammonium acetate/acetonitrile)
  8. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-ade4cc67b45f4d918fc0514a00e8c663
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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