HCID 10101472, compound → HCID 11764742, compound

HRID 644340Notes

Reaction equation

HRID 644340 reaction equation
C([N:8]1[CH2:13][CH2:12][CH:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20](=[O:54])[C@H:21]([NH:33][C:34]([N:36]3[CH2:41][CH2:40][CH:39]([N:42]4[CH2:48][CH2:47][C:46]5[CH:49]=[CH:50][CH:51]=[CH:52][C:45]=5[NH:44][C:43]4=[O:53])[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:54]=[C:20]([N:17]1[CH2:18][CH2:19][N:14]([CH:11]2[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]2)[CH2:15][CH2:16]1)[C@H:21]([NH:33][C:34]([N:36]1[CH2:37][CH2:38][CH:39]([N:42]2[CH2:48][CH2:47][C:46]3[CH:49]=[CH:50][CH:51]=[CH:52][C:45]=3[NH:44][C:43]2=[O:53])[CH2:40][CH2:41]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 10101472HCID 10101472, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 11764742HCID 11764742, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 100 mg (0.14 mmol) 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylic acid [(R)-2-[4-(1-benzyl-piperidin-4-yl)-piperazin-1-yl]-2-oxo-1-(5,6,7,8-tetrahydro-naphthalen-2-ylmethyl)-ethyl]-amide (Example 50) in 10 mL MeOH was hydrogenated in the presence of 20 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-0eacfc883a9042bdb809ddd98dd3432f
Source dataset
uspto-grants-2010_04
Patent number
US07700589B2

Reaction notes

Loading…