HCID 57666543, compound → HCID 57666493, compound

HRID 456011Notes

Reaction equation

HRID 456011 reaction equation
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]2[CH2:11][C:12]([CH3:21])([CH3:20])[S:13](=[O:19])(=[O:18])[C:14]([CH3:17])([CH3:16])[CH:15]=2)=[N:8][CH:9]=1)([O-])=O>CO.[Pd]>[CH3:20][C:12]1([CH3:21])[CH2:11][CH:10]([C:7]2[N:8]=[CH:9][C:4]([NH2:1])=[CH:5][CH:6]=2)[CH2:15][C:14]([CH3:16])([CH3:17])[S:13]1(=[O:19])=[O:18]

Participants

4

Reactant 1

HCID 57666543HCID 57666543, compound

Product 1

HCID 57666493HCID 57666493, compoundYield 64%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 5-nitro-2-(2,2,6,6-tetramethyl-1,1-dioxo-1,2,3,6-tetrahydro-1λ6-thiopyran-4-yl)-pyridine (322 mg, 1.04 mmol, as prepared in the previous step) in MeOH (10 mL) was hydrogenated with 5% Pd/C and 1 atm H2 at RT for 17 h. The mixture was filtered through Celite, and the filter cake was washed with MeOH. The solvents were evaporated in vacuo. The residue was purified on a 25-g Sepra Si 50 SPE column (Isco system: Flow rate=20 mL/min; Eluent=10% EtOAc-hexane for 0-3 min, then 10-50% EtOAc-hexane for 5-30 min, then 50-65% EtOAc-hexane over 40 min, then 65-100% EtOAc-hexane over 40 min) to afford the title compound (187 mg, 64%) as an off-white solid. Mass spectrum (ESI, m/z): Calcd. for C14H22N2O2S, 283.1 (M+H), found 283.1.

Workup

  1. filtrationThe mixture was filtered through Celite
  2. washthe filter cake was washed with MeOH
  3. customThe solvents were evaporated in vacuo
  4. customThe residue was purified on a 25-g Sepra Si 50 SPE column (Isco system
  5. wait10-50% EtOAc-hexane for 5-30 min
  6. wait50-65% EtOAc-hexane over 40 min

Sources & evidence

ORD record
ord-f418b4a4287e454b9463c0804206ef44
Source dataset
uspto-grants-2013_07
Patent number
US08497376B2

Reaction notes

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