HCID 10327754, compound → HCID 10032368, compound

HRID 644343Notes

Reaction equation

HRID 644343 reaction equation
C([N:8]1[CH2:13][CH2:12][N:11]([CH:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:56])[C@H:21]([NH:33][C:34]([N:36]3[CH2:41][CH2:40][CH:39]([N:42]4[C:46]5[CH:47]=[N:48][C:49]6[CH:50]=[CH:51][CH:52]=[CH:53][C:54]=6[C:45]=5[NH:44][C:43]4=[O:55])[CH2:38][CH2:37]3)=[O:35])[CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=4[CH:24]=3)[CH2:16][CH2:15]2)[CH2:10][CH2:9]1)C1C=CC=CC=1.[H][H]>CO.[Pd]>[O:56]=[C:20]([N:17]1[CH2:16][CH2:15][CH:14]([N:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)[CH2:19][CH2:18]1)[C@H:21]([NH:33][C:34]([N:36]1[CH2:41][CH2:40][CH:39]([N:42]2[C:46]3[CH:47]=[N:48][C:49]4[CH:50]=[CH:51][CH:52]=[CH:53][C:54]=4[C:45]=3[NH:44][C:43]2=[O:55])[CH2:38][CH2:37]1)=[O:35])[CH2:22][C:23]1[CH:32]=[CH:31][C:30]2[CH2:29][CH2:28][CH2:27][CH2:26][C:25]=2[CH:24]=1

Participants

5

Reactant 2

HCID 10327754HCID 10327754, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 10032368HCID 10032368, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 300 mg (0.40 mmol) 4-(2-oxo-1,2-dihydro-imidazo[4,5-c]quinolin-3-yl)-piperidine-1-carboxylic acid [(R)-2-[4-(4-benzyl-piperazin-1-yl)-piperidin-1-yl]-2-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-ylmethyl)-ethyl]-amide in 10 mL MeOH was hydrogenated in the presence of 30 mg Pd/C (10%) at 50° C. and 3 bar hydrogen pressure until the calculated volume of hydrogen had been taken up. The catalyst was filtered off, the solvent eliminated under reduced pressure and the residue purified by chromatography on silica gel. The product fractions were evaporated down under reduced pressure and dried.

Workup

  1. filtrationThe catalyst was filtered off
  2. customthe residue purified by chromatography on silica gel
  3. customThe product fractions were evaporated down under reduced pressure
  4. customdried

Sources & evidence

ORD record
ord-630db8dc168e43a2a2c1c039cb243521
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

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