HCID 86722696, compound → HCID 178520321, compound

HRID 1480479Notes

Reaction equation

HRID 1480479 reaction equation
C([N:8]1[CH:12]=[C:11]([CH2:13][CH2:14][NH:15][C:16](=[O:36])[CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=3)=[O:25])[CH2:20][CH2:19]2)[N:10]=[N:9]1)C1C=CC=CC=1.[H][H]>C(O)C>[NH:8]1[CH:12]=[C:11]([CH2:13][CH2:14][NH:15][C:16](=[O:36])[CH2:17][CH:18]2[CH2:23][CH2:22][N:21]([C:24]([O:26][CH2:27][C:28]3[CH:33]=[C:32]([Cl:34])[CH:31]=[C:30]([Cl:35])[CH:29]=3)=[O:25])[CH2:20][CH2:19]2)[N:10]=[N:9]1

Participants

4

Reactant 2

HCID 86722696HCID 86722696, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178520321HCID 178520321, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-dichlorobenzyl 4-(2-((2-(1-benzyl-1H-1,2,3-triazol-4-yl)ethyl)amino)-2-oxoethyl)piperidine-1-carboxylate (81.5 mg, 0.154 mmol) was dissolved in ethanol (4 ml). The solution was then submitted to continuous flow hydrogenation using H-cube hydrogenation apparatus, at 70° C. and 30 bar hydrogen pressure for 2 hours. The resultant solution was concentrated under reduced pressure. Purification was carried out using preparative LC-MS. Product fractions were collected, concentrated under reduced pressure, diluted with ethyl acetate, and washed with water. The organic portion was separated, dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound.

Workup

  1. concentrationThe resultant solution was concentrated under reduced pressure
  2. customPurification
  3. customProduct fractions were collected
  4. concentrationconcentrated under reduced pressure
  5. additiondiluted with ethyl acetate
  6. washwashed with water
  7. customThe organic portion was separated
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-2831194b7c564d6fbb62a026556a34e3
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

Loading…