Hydrogen Peroxide → N-(4-{4-(5-(2-Methoxyethoxy)pyrazin-2-ylsulfinyl)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide

HRID 1465585Notes

Reaction equation

HRID 1465585 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:7]=[CH:8][C:9]([S:12][C:13]2[CH:18]=[C:17]([CH3:19])[C:16]([C:20]3[N:21]=[C:22]([NH:25][C:26](=[O:33])[C:27]4[CH:32]=[CH:31][N:30]=[CH:29][CH:28]=4)[S:23][CH:24]=3)=[C:15]([CH3:34])[CH:14]=2)=[N:10][CH:11]=1.C(OC(=O)C)(=[O:37])C.OO>ClCCl>[CH3:1][O:2][CH2:3][CH2:4][O:5][C:6]1[N:7]=[CH:8][C:9]([S:12]([C:13]2[CH:18]=[C:17]([CH3:19])[C:16]([C:20]3[N:21]=[C:22]([NH:25][C:26](=[O:33])[C:27]4[CH:28]=[CH:29][N:30]=[CH:31][CH:32]=4)[S:23][CH:24]=3)=[C:15]([CH3:34])[CH:14]=2)=[O:37])=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 784Hydrogen PeroxideHCID 7918Acetic AnhydrideHCID 71566783N-(4-{4-(5-(2-Methoxyethoxy)pyrazin-2-ylthio)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide

Product 1

HCID 86690888N-(4-{4-(5-(2-Methoxyethoxy)pyrazin-2-ylsulfinyl)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamideYield 49%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 27 (200.0 mg, 0.41 mmol, 1.0 equiv), acetic anhydride (0.040 mL, 0.45 mmol, 1.1 equiv), 30% hydrogen peroxide (201.1 mg, 5.94 mmol, 4.4 equiv), and silica gel (81.1 mg, 230-400 mesh) in dichloromethane (5.0 mL) was stirred at room temperature for 16 h. The solution was concentrated under reduced pressure, and the residue was re-dissolved in EtOAc (30 mL). The solution was washed with saturated aqueous NaHCO3 (20 mL), dried over MgSO4, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (90% EtOAc in hexanes as eluant) to provide to provide N-(4-{4-(5-(2-methoxyethoxy)pyrazin-2-ylsulfinyl)-2,6-dimethylphenyl}thiazol-2-yl)isonicotinamide (32, 100.3 mg, 0.2 mmol) as yellow solids in 49% yield: 1H NMR (DMSO-d6, 500 MHz) δ 13.05 (s, 1 H), 8.81 (d, J=5.5 Hz, 2 H), 8.68 (s, 1 H), 8.40 (s, 1 H), 7.98 (d, J=5.5 Hz, 2 H), 7.50 (s, 2 H), 7.26 (s, 1 H), 4.47-4.48 (m, 2 H), 3.67-3.69 (m, 2 H), 3.29 (s, 3 H), 2.14 (s, 6 H); ESI-MS: m/z 510.1 (M+H)+.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. dissolutionthe residue was re-dissolved in EtOAc (30 mL)
  3. washThe solution was washed with saturated aqueous NaHCO3 (20 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (90% EtOAc in hexanes as eluant)
  7. customto provide

Sources & evidence

ORD record
ord-0cfa89876a364b949a01df48851061ff
Source dataset
uspto-grants-2015_04
Patent number
US08999983B2

Reaction notes

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