2-Aminothiophenol → HCID 46199088, compound

HRID 1959343Notes

Reaction equation

HRID 1959343 reaction equation
[NH2:1][C:2]1[C:3]([C:19](Cl)=O)=[N:4][C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)=[CH:6][N:7]=1.[NH2:22][C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[SH:29]>C(#N)C>[S:29]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[N:22]=[C:19]1[C:3]1[C:2]([NH2:1])=[N:7][CH:6]=[C:5]([N:8]2[CH2:13][CH2:12][N:11]([S:14]([CH2:17][CH3:18])(=[O:16])=[O:15])[CH2:10][CH2:9]2)[N:4]=1

Participants

4

Reactant 2

HCID 87132-AminothiophenolHCID 86662068HCID 86662068, compound

Product 1

HCID 46199088HCID 46199088, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 3-amino-6-(4-ethylsulfonylpiperazin-1-yl)pyrazine-2-carbonyl chloride (100 mg, 0.2996 mmol) and 2-aminobenzenethiol (112.5 mg, 96.98 μL, 0.8988 mmol) in acetonitrile was heated at 70° C. overnight. The reaction mixture was allowed to cool to RT, filtered and the resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]. The fractions were combined but still contained an impurity. The mixture was therefore purified on silica gel by flash column chromatography (50% EtOAc/Hexanes) to afford the title compound as a bright orange solid (23.2 mg, 20% Yield). 1H NMR (400.0 MHz, DMSO) d 1.24 (3H, t), 3.12 (2H, q), 3.36 masked signal, 3.54 (4H, m), 7.39 (2H, br s), 7.44-7.48 (1H, d), 7.52-7.57 (1H, d), 8.06 (1H, m), 8.11 (1H, m), 8.24 (1H, s) ppm; MS (ES+) 405

Workup

  1. temperatureto cool to RT
  2. filtrationfiltered
  3. customthe resultant residue was purified by reverse phase preparative HPLC [Waters Sunfire C18, 10 uM, 100A column, gradient 10%-95% B (solvent A: 0.05% TFA in water, solvent B: CH3CN) over 16 minutes at 25 mL/min]
  4. customThe mixture was therefore purified on silica gel by flash column chromatography (50% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-af0f17875af046f99e7240c56e3bd3c5
Source dataset
uspto-grants-2013_04
Patent number
US08410112B2

Reaction notes

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