Sodium methanethiolate → HCID 71281396, compound

HRID 335061Notes

Reaction equation

HRID 335061 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH2:8][C:9]2[C:18]3[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=3)[C:12]([O:19]C)=[C:11]([C:21]([NH:23][C@H:24]3[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]3[OH:30])=[O:22])[CH:10]=2)[CH:5]=[CH:4][N:3]=1.[CH3:31][S-:32].[Na+]>CS(C)=O.C(OCC)(=O)C.O>[OH:19][C:12]1[C:13]2[C:18](=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:9]([CH2:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([S:32][CH3:31])[CH:7]=2)=[CH:10][C:11]=1[C:21]([NH:23][C@H:24]1[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]1[OH:30])=[O:22]

Participants

6

Reactant 2

HCID 4378561Sodium methanethiolate2×HCID 86677539HCID 86677539, compound

Product 1

HCID 71281396HCID 71281396, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-[(2-chloropyridin-4-yl)methyl]-N-[(1S,2S)-2-hydroxycyclohexyl]-1-methoxy-2-naphthamide (0.050 g, 0.12 mmol) in 1 mL of DMSO was added sodium thiomethoxide (0.025 g, 0.35 mmol). The mixture was heated in a sealed tube at 100° C. for 18 hours, then cooled to room temperature. Additional sodium thiomethoxide (0.025 g, 0.35 mmol) was added, and the reaction was heated to 120° C. for 3 hours, then recooled to room temperature and diluted with ethyl acetate and water. The aqueous layer was extracted 3× with ethyl acetate and the combined organic fractions were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to provide 1-hydroxy-N-[(1S,2S)-2-hydroxycyclohexyl]-4-{[2-(methylthio)pyridin-4-yl]methyl}-2-naphthamide that gave a mass ion (ES+) of 423.0 for [M+H]+.

Workup

  1. temperaturecooled to room temperature
  2. temperaturethe reaction was heated to 120° C. for 3 hours
  3. customrecooled to room temperature
  4. extractionThe aqueous layer was extracted 3× with ethyl acetate
  5. washthe combined organic fractions were washed with brine
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8e195b2f2e27477cafa0e700037a75c9
Source dataset
uspto-grants-2014_11
Patent number
US08883850B2

Reaction notes

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