HCID 66597913, compound → HCID 66760824, compound

HRID 1518645Notes

Reaction equation

HRID 1518645 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].C([O:15][C:16]1[CH:17]=[CH:18][C:19]([C@@H:27]([OH:63])[CH2:28][NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]2[CH:40]=[CH:41][C:42]([C:57]3[CH:62]=[CH:61][CH:60]=[CH:59][CH:58]=3)=[C:43]([NH:45][C:46]([O:48][CH:49]3[CH2:54][CH2:53][N+:52]([CH3:56])([CH3:55])[CH2:51][CH2:50]3)=[O:47])[CH:44]=2)=[C:20]2[C:25]=1[NH:24][C:23](=[O:26])[CH:22]=[CH:21]2)C1C=CC=CC=1>CO.[C].[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([O-:5])=[O:4].[OH:63][C@H:27]([C:19]1[CH:18]=[CH:17][C:16]([OH:15])=[C:25]2[C:20]=1[CH:21]=[CH:22][C:23](=[O:26])[NH:24]2)[CH2:28][NH:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH2:38][C:39]1[CH:40]=[CH:41][C:42]([C:57]2[CH:58]=[CH:59][CH:60]=[CH:61][CH:62]=2)=[C:43]([NH:45][C:46]([O:48][CH:49]2[CH2:50][CH2:51][N+:52]([CH3:56])([CH3:55])[CH2:53][CH2:54]2)=[O:47])[CH:44]=1

Participants

4

Reactant 1

HCID 66597913HCID 66597913, compound

Product 1

HCID 66760824HCID 66760824, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

The obtained 4-({[5-(9-[{(2R)-[8-(benzyloxy)-2-oxo-1,2-dihydroquinolin-5-yl]-2-hydroxyethyl}amino]nonyl)-2-phenylphenyl]carbamoyl}oxy)-1,1-dimethylpiperidin-1-ium trifluoroacetate was dissolved in methanol (5 mL), 10% palladium-carbon (50 mg) was added thereto, and the mixture was stirred under a hydrogen atmosphere at room temperature for 2 hours. The reaction solution was filtered through celite and the filtrate was concentrated under reduced pressure. The residue was purified by HPLC fractionation to obtain 4-({[5-(9-{[(2R)-2-hydroxy-2-(8-hydroxy-2-oxo-1,2-dihydroquinolin-5-yl)ethyl]amino}nonyl)-2-phenylphenyl]carbamoyl}oxy)-1,1-dimethylpiperidin-1-ium trifluoroacetate (12.79 mg).

Workup

  1. filtrationThe reaction solution was filtered through celite
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by HPLC fractionation

Sources & evidence

ORD record
ord-a202d3dff2e74614a50a00e69ee14a52
Source dataset
uspto-grants-2015_07
Patent number
US09072734B2

Reaction notes

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