Sodium Bicarbonate → N-[1-(4-Chloro-3-fluorobenzyl)-4-piperidinyl]-3-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]propanamide

HRID 1070513Notes

Reaction equation

HRID 1070513 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.[Cl:17][C:18]1[CH:31]=[CH:30][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH2:29])[CH2:25][CH2:24]2)=[CH:20][C:19]=1[F:32].C(=O)([O-])O.[Na+]>ClCCl>[Cl:17][C:18]1[CH:31]=[CH:30][C:21]([CH2:22][N:23]2[CH2:28][CH2:27][CH:26]([NH:29][C:14](=[O:16])[CH2:13][CH2:12][C:10]3[O:9][N:8]=[C:7]([C:2]4[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=4)[N:11]=3)[CH2:25][CH2:24]2)=[CH:20][C:19]=1[F:32]

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 31643283-(3-pyridin-2-yl-1,2,4-oxadiazol-5-yl)propanoic acidHCID 223962051-(4-Chloro-3-fluorobenzyl)-4-piperidinamine

Product 1

HCID 22396154N-[1-(4-Chloro-3-fluorobenzyl)-4-piperidinyl]-3-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]propanamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3-[3-(2-Pyridinyl)-1,2,4-oxadiazol-5-yl]propanoic acid (0.136 g) and N,N′-carbonyldiimidazole (0.114 g) were stirred in dichloromethane (10 ml) under nitrogen for 1 hour. 1-(4-Chloro-3-fluorobenzyl)-4-piperidinamine (0.150 g) was then added and left to stir for 2 hours. 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 was triturated with diethyl ether which caused product the to crystallise. After filtration, the product was washed with diethyl ether and dried to N-[1-(4-chloro-3-fluorobenzyl)-4-piperidinyl]-3-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]propanamide. m.p. 132° C.

Workup

  1. waitleft
  2. extractionbeing extracted three times with dichloromethane
  3. washThe pooled organic phases were washed once with water, once with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customthe solvent removed under reduced pressure
  7. customto leave an oil
  8. customThis was triturated with diethyl ether which
  9. customto crystallise
  10. filtrationAfter filtration
  11. washthe product was washed with diethyl ether
  12. dry with materialdried to N-[1-(4-chloro-3-fluorobenzyl)-4-piperidinyl]-3-[3-(2-pyridinyl)-1,2,4-oxadiazol-5-yl]propanamide

Sources & evidence

ORD record
ord-58379b9279144aaeacbf622b872cb3d4
Source dataset
uspto-grants-2005_06
Patent number
US06903085B1

Reaction notes

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