HCID 53757231, compound → HCID 53700152, compound

HRID 1837939Notes

Reaction equation

HRID 1837939 reaction equation
[C:1]([O:5][C:6](=[O:34])[CH:7]=[C:8]([C:25]1[S:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=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:26][C:27]2[CH:33]=[CH:32][CH:31]=[CH:30][C:28]=2[N:29]=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 53757231HCID 53757231, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53700152HCID 53700152, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

To a stirred suspension of 10% palladium on carbon (50 mg) in methanol (5 mL) was added a solution of 3-(benzothiazol-2-yl)-9-(5,6,7,8-tetrahydro-[1,8]naphthyridin-2-yl)-non-2-enoic acidtert-butyl ester 29-7c (190 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 4:1 hexanes/acetone to give 29-8c 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 4:1 hexanes/acetone

Sources & evidence

ORD record
ord-5e643a3ab69e4e03b98376d8ab96126e
Source dataset
uspto-grants-2004_08
Patent number
US06784190B2

Reaction notes

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