Ethanol → HCID 58306959, compound

HRID 1909910Notes

Reaction equation

HRID 1909910 reaction equation
Cl[C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:18]([NH:20][C@H:21]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)[CH3:22])=[O:19])[CH:11]=[CH:10]2)=[CH:4][CH:3]=1.N1CCCCC1.[CH2:38]([OH:40])[CH3:39]>>[CH2:38]([O:40][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]2[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][C:16]=3[C:18]([NH:20][C@H:21]([C:23]3[CH:31]=[CH:30][C:26]([C:27]([OH:29])=[O:28])=[CH:25][CH:24]=3)[CH3:22])=[O:19])[CH:11]=[CH:10]2)=[CH:4][CH:3]=1)[CH3:39]

Participants

4

Reactant 3

HCID 702EthanolHCID 8082PiperidineHCID 58307045HCID 58307045, compound

Product 1

HCID 58306959HCID 58306959, compound

Procedure

To 4-{(1S)-1-[({1-[(6-chloropyridin-3-yl)methyl]-1H-indol-7-yl}carbonyl)amino]ethyl}benzoic acid (95 mg) were added ethanol (2.0 mL) and piperidine (65 μL), followed by stirring at room temperature overnight. After concentration under reduced pressure, DMSO (1.0 mL), piperidine (65 μL), and potassium tert-butoxide (61 mg) were added thereto, followed by stirring at 80° C. for 2 hours. To the reaction mixture was added a 10% aqueous citric acid solution (10 mL), followed by extraction with ethyl acetate. The obtained organic layer was washed with water, dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform/methanol=99/1-95/5) to obtain 4-{(1S)-1-[({1-[(6-ethoxypyridin-3-yl)methyl]-1H-indol-7-yl}carbonyl)amino]ethyl}benzoic acid (9.0 mg).

Workup

  1. concentrationAfter concentration under reduced pressure, DMSO (1.0 mL), piperidine (65 μL), and potassium tert-butoxide (61 mg)
  2. additionwere added
  3. stirringby stirring at 80° C. for 2 hours
  4. additionTo the reaction mixture was added a 10% aqueous citric acid solution (10 mL)
  5. extractionfollowed by extraction with ethyl acetate
  6. washThe obtained organic layer was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe residue was purified by silica gel column chromatography (chloroform/methanol=99/1-95/5)

Sources & evidence

ORD record
ord-a31697ef83234f8392b5862b5319fb57
Source dataset
uspto-grants-2013_12
Patent number
US08598355B2

Reaction notes

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