HCID 68676853, compound → HCID 57674071, compound

HRID 491142Notes

Reaction equation

HRID 491142 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]([CH2:33][C:34]3[CH:39]=[C:38]([CH3:40])[C:37]([O:41]CC4C=CC=CC=4)=[C:36](Cl)[CH:35]=3)[C:19](=[O:32])[N:20]3[CH2:25][CH2:24][N:23]([CH:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH2:22][CH2:21]3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:50]=[CH:51][CH:52]=[CH:53][C:4]=2[NH:3]1.[H][H]>CO.C(N(CC)CC)C.[Pd]>[O:1]=[C:2]1[N:8]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C@H:18]([CH2:33][C:34]3[CH:35]=[CH:36][C:37]([OH:41])=[C:38]([CH3:40])[CH:39]=3)[C:19](=[O:32])[N:20]3[CH2:21][CH2:22][N:23]([CH:26]4[CH2:27][CH2:28][O:29][CH2:30][CH2:31]4)[CH2:24][CH2:25]3)=[O:16])[CH2:11][CH2:10]2)[CH2:7][CH2:6][C:5]2[CH:50]=[CH:51][CH:52]=[CH:53][C:4]=2[NH:3]1

Participants

6

Reactant 2

HCID 68676853HCID 68676853, compoundHCID 178418361HCID 178418361, compound2×

Product 1

HCID 57674071HCID 57674071, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8471TriethylamineSolvent

Procedure

A suspension of 108 mg (0.15 mmol) (R)-1-(4-benzyloxy-3-chloro-5-methyl-benzyl)-2-oxo-2-[4-(tetrahydropyran-4-yl)-piperazin-1-yl]-ethyl 4-(2-oxo-1,2,4,5-tetrahydro-1,3-benzodiazepin-3-yl)-piperidine-1-carboxylate and 30 mg 10% Pd/C in 10 mL MeOH and 0.5 mL triethylamine was hydrogenated at RT and 3000 hPa hydrogen pressure until the theoretical amount of hydrogen had been taken up. The catalyst was filtered off, the residue was dissolved in 1 mL DMF and purified by HPLC. The fractions containing the product were combined and lyophilised.

Workup

  1. customwas hydrogenated at RT
  2. filtrationThe catalyst was filtered off
  3. dissolutionthe residue was dissolved in 1 mL DMF
  4. custompurified by HPLC
  5. additionThe fractions containing the product

Sources & evidence

ORD record
ord-bb35ce3a97994be18d072959b63687c3
Source dataset
uspto-grants-2009_05
Patent number
US07528129B2

Reaction notes

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