Water → HCID 178487392, compound

HRID 2409980Notes

Reaction equation

HRID 2409980 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25](=[N:27][OH:28])[NH2:26])[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[NH:9]2)=[CH:5][CH:4]=1.N1C=CC=CC=1.[S:35](Cl)(Cl)=[O:36].O>O1CCCC1.C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:11]=[C:10]2[C:6]([C:7]([CH2:18][C:19]3[N:24]=[C:23]([C:25]4[NH:26][S:35](=[O:36])[O:28][N:27]=4)[CH:22]=[CH:21][CH:20]=3)=[C:8]([C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=3)[NH:9]2)=[CH:5][CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 136344372HCID 136344372, compound

Product 1

HCID 178487392HCID 178487392, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, a solution of 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxamidoxime (277 mg) and pyridine (0.121 mL) in tetrahydrofuran (3.1 mL) was ice-cooled. A solution of thionyl chloride (0.055 mL) in methylene chloride (0.62 mL) was added dropwise thereto, and this mixture was stirred at the same temperature for 2 hours. To the reaction mixture was added water, followed by extraction with dichloromethane. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane) to obtain the title compound (60.9 mg). 1H-NMR (DMSO-d6) δ ppm: 3.78 (3H, s), 4.44 (2H, s), 6.64 (1H, dd, J=2.3, 8.5 Hz), 6.89 (1H, d, J=2.3 Hz), 7.18 (1H, dd, J=1.8, 7.3 Hz), 7.26-7.38 (2H, m), 7.41-7.54 (2H, m), 7.59-7.66 (2H, m), 7.79-7.90 (2H, m), 11.23 (1H, s), 11.80-12.20 (1H, br). ESI-MS (m/z): 419 (M+H)+

Workup

  1. temperaturecooled
  2. extractionfollowed by extraction with dichloromethane
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane)

Sources & evidence

ORD record
ord-b68c2b74db904b19a671b8ff6b56308c
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

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