HCID 86651279, compound → HCID 86651278, compound

HRID 1515045Notes

Reaction equation

HRID 1515045 reaction equation
[CH2:1]([O:3][P:4](/[CH:9]=[CH:10]/[C:11]1[CH:16]=[C:15]([CH3:17])[C:14]([C:18]2[NH:22][C:21]3[CH:23]=[C:24]([C:27](=[O:39])[NH:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)[CH:25]=[CH:26][C:20]=3[N:19]=2)=[C:13]([CH3:40])[CH:12]=1)(=[O:8])[O:5][CH2:6][CH3:7])[CH3:2]>CCO.[Pd]>[CH2:6]([O:5][P:4]([CH2:9][CH2:10][C:11]1[CH:12]=[C:13]([CH3:40])[C:14]([C:18]2[NH:22][C:21]3[CH:23]=[C:24]([C:27](=[O:39])[NH:28][C:29]4[CH:38]=[CH:37][C:36]5[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=5)[N:30]=4)[CH:25]=[CH:26][C:20]=3[N:19]=2)=[C:15]([CH3:17])[CH:16]=1)(=[O:8])[O:3][CH2:1][CH3:2])[CH3:7]

Participants

4

Reactant 1

HCID 86651279HCID 86651279, compound

Product 1

HCID 86651278HCID 86651278, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A solution of ((E)-2-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-vinyl)-phosphonic acid diethyl ester (300 mg, 0.54 mmol) in EtOH (20 mL) was hydrogenated at one atm over Pd/C (225 mg) for 3 hours. The catalyst was filtered through Celite and was washed with EtOH. The solvent was removed under reduced pressure to give (2-{3,5-dimethyl-4-[6-(quinolin-2-ylcarbamoyl)-1H-benzoimidazol-2-yl]-phenyl}-ethyl)-phosphonic acid diethyl ester as a red solid.

Workup

  1. filtrationThe catalyst was filtered through Celite
  2. washwas washed with EtOH
  3. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-60d200fd8a07417b96735996f2b8e4cd
Source dataset
uspto-grants-2012_07
Patent number
US08222248B2

Reaction notes

Loading…