HCID 68577326, compound → HCID 68577392, compound

HRID 446887Notes

Reaction equation

HRID 446887 reaction equation
C([N:8]1[CH2:13][C@@H:12]2[CH2:14][CH:9]1[CH2:10][N:11]2[C:15](=[O:43])[CH2:16][NH:17][C:18](=[O:42])[C:19]1[CH:24]=[CH:23][C:22]([S:25](=[O:41])(=[O:40])[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[CH:21][CH:20]=1)C1C=CC=CC=1>C(O)(=O)C.[Pd]>[C@H:12]12[CH2:14][CH:9]([NH:8][CH2:13]1)[CH2:10][N:11]2[C:15](=[O:43])[CH2:16][NH:17][C:18](=[O:42])[C:19]1[CH:20]=[CH:21][C:22]([S:25](=[O:40])(=[O:41])[NH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=2[O:33][C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)=[CH:23][CH:24]=1

Participants

4

Reactant 1

HCID 68577326HCID 68577326, compound

Product 1

HCID 68577392HCID 68577392, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A stirred mixture of N-[2-((S)-5-benzyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-2-oxo-ethyl]-4-(2-phenoxy-phenylsulfamoyl)-benzamide (Example 2.61) (46 mg, 0.077 mmol) and 10% Pd/C (10 mg) in acetic acid (5 mL) was hydrogenated at 5 bar at room temperature for 2 h. The catalyst was filtered off and the filtrate was concentrated in vacuo. The residue was purified by column chromatography using Kieselgel 60 (0.015-0.040 mm) (Merck) as adsorbent and chloroform:methanol:ammonium hydroxide=9:1:0.1 as eluent to yield 37.9 mg (97%) of the title compound. MS (EI) 507.1 (MH+).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-c4216824bbad49d79db15666b9b4c556
Source dataset
uspto-grants-2013_07
Patent number
US08481527B2

Reaction notes

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