Hydrochloric Acid → HCID 178487106, compound

HRID 2400297Notes

Reaction equation

HRID 2400297 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:10]([CH2:20][C:21]2[N:26]=[C:25]([C:27](=[N:29][OH:30])[NH2:28])[CH:24]=[CH:23][CH:22]=2)[C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2.[C:31](N1C=CN=C1)(N1C=CN=C1)=[S:32].N12CCCN=C1CCCCC2.Cl>C(#N)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[N:10]([CH2:20][C:21]2[N:26]=[C:25]([C:27]3[NH:28][C:31](=[S:32])[O:30][N:29]=3)[CH:24]=[CH:23][CH:22]=2)[C:11]2[C:16]([CH:17]=1)=[CH:15][C:14]([O:18][CH3:19])=[CH:13][CH:12]=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 802641,1'-ThiocarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 136338093HCID 136338093, compound

Product 1

HCID 178487106HCID 178487106, compoundYield 100.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 6-[2-(2,5-difluorophenyl)-5-methoxyindol-1-ylmethyl]pyridine-2-carboxamidoxime (63 mg) in acetonitrile (1.54 mL) were successively added 1,1′-thiocarbonyldiimidazole (41 mg) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.092 mL), followed by stirring at room temperature for 3 hours. To the reaction mixture was added 1 mol/L hydrochloric acid, followed by extraction with ethyl acetate. The organic layer was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively, dried over anhydrous sodium sulfate, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-methanol) to obtain the title compound (70 mg). 1H-NMR (DMSO-d6) δ ppm: 3.77 (3H, s), 5.41 (2H, s), 6.50-6.60 (1H, m), 6.67 (1H, s), 6.80 (1H, dd, J=2.4, 9.0 Hz), 7.15 (1H, d, J=2.4 Hz), 7.25-7.45 (3H, m), 7.50-7.60 (1H, m), 7.65-7.80 (2H, m). ESI-MS (m/z): 451 (M+H)+

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe organic layer was washed with 1 mol/L hydrochloric acid, saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (eluting solvent: ethyl acetate-methanol)

Sources & evidence

ORD record
ord-7cfd5866e05641ecb2075d1c7274ee4e
Source dataset
uspto-grants-2014_08
Patent number
US08796247B2

Reaction notes

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