Pyridine → HCID 16722858, compound

HRID 2421150Notes

Reaction equation

HRID 2421150 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH2:26])[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1.C[Si]([N-][Si](C)(C)C)(C)C.[K+].[CH:37]([S:40](Cl)(=[O:42])=[O:41])([CH3:39])[CH3:38].N1C=CC=CC=1>O1CCCC1>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:26][S:40]([CH:37]([CH3:39])[CH3:38])(=[O:42])=[O:41])[CH:6]=[CH:7][C:8]=1[C:9]1[O:10][C:11]([C:14]2[C:15]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)=[N:16][O:17][C:18]=2[CH3:19])=[N:12][N:13]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 824082-Propanesulfonyl chloride2×HCID 3251421Potassium bis(trimethylsilyl)amideHCID 167225873-Methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine

Product 1

HCID 16722858HCID 16722858, compoundYield 11.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-methoxy-4-[5-(5-methyl-3-phenyl-isoxazol-4-yl)-[1,3,4]oxadiazol-2-yl]-phenylamine (200 mg, 0.57 mmol) in tetrahydrofuran (5 mL) was added at 0° C. potassium bis(trimethylsilyl)amide (0.91 M in tetrahydrofuran, 1.51 mL, 1.38 mmol). After stirring for 15 min at this temperature isopropylsulfonyl chloride (319 mg, 2.24 mmol) was added and stirring was continued at ambient temperature for 76 h. Further isopropylsulfonyl chloride (107 mg, 0.75 mmol) and pyridine (454 mg, 5.74) were added and stirring was continued for 24 h. The resulting suspension was extracted with ethyl acetate (20 mL) and the combined organic layers were washed with aqueous sodium carbonate (saturated). Drying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane 50:30:20 to 20:60:20) afforded the title compound (29 mg, 11%) as a yellow solid. MS: m/e 455.2 [M+H]+.

Workup

  1. additionwas added
  2. stirringstirring
  3. waitwas continued for 24 h
  4. extractionThe resulting suspension was extracted with ethyl acetate (20 mL)
  5. washthe combined organic layers were washed with aqueous sodium carbonate (saturated)
  6. dry with materialDrying over sodium sulfate and purification by chromatography (SiO2, heptane:ethyl acetate:dichloromethane 50:30:20 to 20:60:20)

Sources & evidence

ORD record
ord-3f7d31880a784abcbd24bd966a91d701
Source dataset
uspto-grants-2011_06
Patent number
US07956074B2

Reaction notes

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