HCID 178418361, compound → HCID 178425367, compound

HRID 642825Notes

Reaction equation

HRID 642825 reaction equation
[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:40][C:41]3[CH:49]=[C:48]([CH3:50])[C:44]4[NH:45][CH:46]=[N:47][C:43]=4[CH:42]=3)[C:19]([N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:32][CH2:31][N:30](CC5C=CC=CC=5)[CH2:29][CH2:28]4)[CH2:23][CH2:22]3)=[O:20])=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:51]=[CH:52][CH:53]=[CH:54][C:4]=2[NH:3]1.[H][H]>CO.[Pd]>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:10][CH2:11][N:12]([C:15]([O:17][C@H:18]([CH2:40][C:41]3[CH:49]=[C:48]([CH3:50])[C:44]4[NH:45][CH:46]=[N:47][C:43]=4[CH:42]=3)[C:19](=[O:20])[N:21]3[CH2:26][CH2:25][CH:24]([N:27]4[CH2:28][CH2:29][NH:30][CH2:31][CH2:32]4)[CH2:23][CH2:22]3)=[O:16])[CH2:13][CH2:14]2)[CH2:7][CH2:6][C:5]2[CH:51]=[CH:52][CH:53]=[CH:54][C:4]=2[NH:3]1

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178425368HCID 178425368, compound

Product 1

HCID 178425367HCID 178425367, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

67 mg (0.08 mmol) (R)-2-[4-(4-benzyl-piperazin-1-yl)-piperidin-1-yl]-1-(7-methyl-1H-benzimidazol-5-ylmethyl)-2-oxo-ethyl 4-(2-oxo-1,2,4,5,-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate were dissolved in 10 mL MeOH and combined with 30 mg 10% Pd/C. The mixture was hydrogenated for 3 h in a Parr apparatus at 50° C. and 50 psi hydrogen pressure. Then the catalyst was filtered off and the filtrate was evaporated down i.vac. The residue was purified by HPLC, the fractions containing the product were combined and lyophilised.

Workup

  1. filtrationThen the catalyst was filtered off
  2. customthe filtrate was evaporated down i.vac
  3. customThe residue was purified by HPLC
  4. additionthe fractions containing the product

Sources & evidence

ORD record
ord-4b98a5f73b3945a4880b6513e526ce6a
Source dataset
uspto-grants-2010_04
Patent number
US07696195B2

Reaction notes

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