2-Mercaptoethanol → HCID 22036258, compound

HRID 991696Notes

Reaction equation

HRID 991696 reaction equation
[OH-].[Na+].[SH:3][CH2:4][CH2:5][OH:6].Cl[C:8]1[C:13]([N:14]2[CH2:19][CH2:18][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:16][CH2:15]2)=[N:12][CH:11]=[CH:10][N:9]=1>O.O1CCOCC1>[OH:6][CH2:5][CH2:4][S:3][C:8]1[C:13]([N:14]2[CH2:15][CH2:16][N:17]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:18][CH2:19]2)=[N:12][CH:11]=[CH:10][N:9]=1

Participants

6

Reactant 3

HCID 15672-MercaptoethanolHCID 14798Sodium HydroxideHCID 11150691Tert-butyl 4-(3-chloropyrazin-2-yl)piperazine-1-carboxylate

Product 1

HCID 22036258HCID 22036258, compoundYield 65.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent2×

Conditions

Temperature
100 °C

Procedure

Sodium hydroxide (0.92 g, 23 mmol) was dissolved in water (9 mL) and dioxane (15 mL). 2-Mercaptoethanol (0.54 mL, 7.7 mmol) was added while stirring and 2-chloro-3-(4-tert-butoxycarbonyl-1-piperazinyl)pyrazine (2.3 g, 7.7 mmol, from Example 52, step 1) in dioxane (10 mL) was added. The reaction mixture was heated at 100° C. for 22 h. After cooling to room temperature, it was extracted with EtOAc. The organic layer was dried (K2CO3) and the solvent was removed under reduced pressure. The residue was purified by chromatography on silica gel using hexane/ EtOAc (1:1) as eluent to give 1.71 g (65%) of the title compound as an orange oil. MS m/z 341 (M+H)+.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionit was extracted with EtOAc
  3. dry with materialThe organic layer was dried (K2CO3)
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by chromatography on silica gel

Sources & evidence

ORD record
ord-1f19a787c987440cbfc9773f3910643c
Source dataset
uspto-grants-2002_10
Patent number
US06465467B1

Reaction notes

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