HCID 86722694, compound → HCID 178520492, compound

HRID 1480475Notes

Reaction equation

HRID 1480475 reaction equation
C([N:8]1[CH:12]=[C:11]([CH2:13][NH:14][C:15](=[O:36])[CH2:16][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][NH:14][C:15](=[O:36])[CH2:16][CH2:17][CH:18]2[CH2:19][CH2:20][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])[CH2:22][CH2:23]2)[N:10]=[N:9]1

Participants

4

Reactant 2

HCID 86722694HCID 86722694, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 178520492HCID 178520492, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3,5-dichlorobenzyl 4-(3-(((1-benzyl-1H-1,2,3-triazol-4-yl)methyl)amino)-3-oxopropyl)piperidine-1-carboxylate (51 mg, 0.096 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. After 90 mins the solution was concentrated and the residue purified using preparative LC-MS. Product fractions were collected, concentrated under reduced pressure, diluted with ethyl acetate, and extracted with water. The organics were separated, dried over MgSO4, filtered, and concentrated under reduced pressure to give the title compound.

Workup

  1. customat 70° C.
  2. concentrationAfter 90 mins the solution was concentrated
  3. customthe residue purified
  4. customProduct fractions were collected
  5. concentrationconcentrated under reduced pressure
  6. additiondiluted with ethyl acetate
  7. extractionextracted with water
  8. customThe organics were separated
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5fa5c6f6632c4a11900d1fa960f16e68
Source dataset
uspto-grants-2016_08
Patent number
US09409895B2

Reaction notes

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