4-(3-(3,6-Dihydro-2H-thiopyran-4-YL)pyrazin-2-yloxy)-N-methoxy-N-methylbenzamide → N-Methoxy-N-methyl-4-(3-(tetrahydro-2H-thiopyran-4-YL)pyrazin-2-yloxy)benzamide

HRID 2192006Notes

Reaction equation

HRID 2192006 reaction equation
[S:1]1[CH2:6][CH:5]=[C:4]([C:7]2[C:8]([O:13][C:14]3[CH:25]=[CH:24][C:17]([C:18]([N:20]([O:22][CH3:23])[CH3:21])=[O:19])=[CH:16][CH:15]=3)=[N:9][CH:10]=[CH:11][N:12]=2)[CH2:3][CH2:2]1>CO.[Pd]>[CH3:23][O:22][N:20]([CH3:21])[C:18](=[O:19])[C:17]1[CH:24]=[CH:25][C:14]([O:13][C:8]2[C:7]([CH:4]3[CH2:3][CH2:2][S:1][CH2:6][CH2:5]3)=[N:12][CH:11]=[CH:10][N:9]=2)=[CH:15][CH:16]=1

Participants

4

Reactant 1

HCID 593513734-(3-(3,6-Dihydro-2H-thiopyran-4-YL)pyrazin-2-yloxy)-N-methoxy-N-methylbenzamide

Product 1

HCID 59351159N-Methoxy-N-methyl-4-(3-(tetrahydro-2H-thiopyran-4-YL)pyrazin-2-yloxy)benzamide

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 23938PalladiumSolvent

Procedure

A solution of 4-(3-(3,6-dihydro-2H-thiopyran-4-yl)pyrazin-2-yloxy)-N-methoxy-N-methylbenzamide (0.500 g, 1.399 mmol) in MeOH (10 ml) was hydrogenated at RT in 10% Pd/C (0.200 mg) in 72 h. The solid was filtered off, and the filtrate was concentrated and purified by ISCO (3% MeOH/DCM) to give the title compound. MS [M+1]: 360.1.

Workup

  1. filtrationThe solid was filtered off
  2. concentrationthe filtrate was concentrated
  3. custompurified by ISCO (3% MeOH/DCM)

Sources & evidence

ORD record
ord-094cb4862fe244fab9b9f0084e047057
Source dataset
uspto-grants-2012_12
Patent number
US08329700B2

Reaction notes

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