HCID 23222130, compound → HCID 19082235, compound

HRID 265285Notes

Reaction equation

HRID 265285 reaction equation
Cl.[OH:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:13][CH2:14][NH:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][O:22][CH2:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)=[C:7]2[C:11]=1[NH:10][C:9](=[O:12])[CH2:8]2>[Ni].C(O)C>[C:25]1([CH2:24][CH2:23][O:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][N:15]([CH2:14][CH2:13][C:6]2[CH:5]=[CH:4][C:3]([O:2][CH2:13][C:6]3[CH:7]=[CH:11][CH:3]=[CH:4][CH:5]=3)=[C:11]3[C:7]=2[CH2:8][C:9](=[O:12])[NH:10]3)[CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

Participants

4

Reactant 1

HCID 23222130HCID 23222130, compound

Product 1

HCID 19082235HCID 19082235, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (1.5 g) was added to a solution of the compound from step d) (2.1 g) in dry ethanol (60 ml). The mixture was heated to reflux for 1 hour, the catalyst was removed by filtration and the filtrate evaporated under reduced pressure. Trituration with ether gave an off-white solid which was purified by reverse phase HPLC (SiO2) using methanol:chloroform as eluant. Recrystallisation from isopropyl alcohol gave the subtitled compound as a buff coloured solid.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux for 1 hour
  3. customthe catalyst was removed by filtration
  4. customthe filtrate evaporated under reduced pressure
  5. customTrituration with ether gave an off-white solid which
  6. customwas purified by reverse phase HPLC (SiO2)
  7. customRecrystallisation from isopropyl alcohol

Sources & evidence

ORD record
ord-39365960e7674b51b8c0bf974702b54c
Source dataset
uspto-grants-1997_07
Patent number
US05648370

Reaction notes

Loading…