HCID 86616527, compound → HCID 69409982, compound

HRID 853921Notes

Reaction equation

HRID 853921 reaction equation
[N:1]1([S:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH:18]([CH3:24])[CH:19]([N:21]=[N+]=[N-])[CH3:20])[C:13](=[O:25])[C:12]23[O:30][CH2:29][CH2:28][CH2:27][O:26]2)(=[O:8])=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1>CO.[Pd]>[N:1]1([S:6]([C:9]2[CH:10]=[C:11]3[C:15](=[CH:16][CH:17]=2)[N:14]([CH:18]([CH3:24])[CH:19]([NH2:21])[CH3:20])[C:13](=[O:25])[C:12]23[O:30][CH2:29][CH2:28][CH2:27][O:26]2)(=[O:7])=[O:8])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 1

HCID 86616527HCID 86616527, compound

Product 1

HCID 69409982HCID 69409982, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture of 3-[5′-{[pyrrolidin-1-yl]sulfonyl}-2′-oxospiro[1,3-dioxane-2,3′-indol]-1′(2′H)-yl]-2-azidobutane (0.16 g, 0.37 mmoles) and 10% Pd/C in methanol (5 ml) was stirred under a H2 atmosphere (1 atmosphere) overnight at room temperature. The reaction mixture was filtered, and concentrated. The crude product was purified by flash chromatography on silica gel using 40% EtOAc/hexane followed by 1% CH3OH/EtOAc to give the title compound as an off white solid (0.06 g, 40% yield). NMR (400 MHz, DMSO-d6): consistent. MS: (API-ES+) m/z 410 [M+H].

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationconcentrated
  3. customThe crude product was purified by flash chromatography on silica gel using 40% EtOAc/hexane

Sources & evidence

ORD record
ord-fbfbea27a2a148a4a5dbb9130c567bff
Source dataset
uspto-grants-2007_08
Patent number
US07256198B2

Reaction notes

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