HCID 54055743, compound → HCID 54055976, compound

HRID 379280Notes

Reaction equation

HRID 379280 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH:7]=[C:8]([C:25]1[S:29][C:28]2[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=2[CH:26]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][NH:18][C:17]=2[N:16]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>[Pd].CO.C(O)C>[C:1]([O:5][C:6](=[O:34])[CH2:7][CH:8]([C:25]1[S:29][C:28]2[CH:30]=[CH:31][CH:32]=[CH:33][C:27]=2[CH:26]=1)[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]1[CH:24]=[CH:23][C:22]2[CH2:21][CH2:20][CH2:19][NH:18][C:17]=2[N:16]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 2

HCID 54055743HCID 54055743, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 54055976HCID 54055976, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a stirred suspension of 10% palladium on carbon (45 mg) in methanol (5 mL) was added a solution of 3-(benzo[b]thiophen-2-yl)-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-non-2-enoic acid tert-butyl ester 29-7b (220 mg) in ethanol (5 mL) and the mixture was subjected to an atmosphere of hydrogen for 48 hours. The reaction mixture was filtered through Celite and concentrated at reduced pressure. The resulting oil was purified by flash column chromatography over silica gel with 9:1 ethyl acetate/methanol to give 29-8b as a colorless oil.

Workup

  1. filtrationThe reaction mixture was filtered through Celite
  2. concentrationconcentrated at reduced pressure
  3. customThe resulting oil was purified by flash column chromatography over silica gel with 9:1 ethyl acetate/methanol

Sources & evidence

ORD record
ord-690cdeaaa5a541f6b5f8362962597bef
Source dataset
uspto-grants-2001_10
Patent number
US06297249B1

Reaction notes

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