Hydrochloric Acid → HCID 135981223, compound

HRID 2409976Notes

Reaction equation

HRID 2409976 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.[C:29](N1C=CN=C1)(N1C=CN=C1)=[O:30].C1CCN2C(=NCCC2)CC1.Cl>O1CCCC1>[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][C:29](=[O:30])[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

6

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-Carbonyldiimidazole2×HCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene2×HCID 136344372HCID 136344372, compound

Product 1

HCID 135981223HCID 135981223, compoundYield 86.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under an argon atmosphere, to a solution of 6-(6-methoxy-2-phenyl-1H-indol-3-ylmethyl)pyridine-2-carboxamidoxime (46.9 mg) in tetrahydrofuran (0.63 mL) were added 1,1′-carbonyldiimidazole (24.5 mg) and 1,8-diazabicyclo[5,4,0]-7-undecene (0.019 mL), and this mixture was stirred at room temperature for 3 hours. 1,1′-Carbonyldiimidazole (16.3 mg) was added thereto, followed by stirring for 80 minutes. Then, 1,8-diazabicyclo[5,4,0]-7-undecene (0.019 mL) was added thereto, followed by stirring for additional 1 hour. 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, a 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: methanol-dichloromethane) to obtain the title compound (43.2 mg).

Workup

  1. stirringby stirring for 80 minutes
  2. stirringby stirring for additional 1 hour
  3. extractionfollowed by extraction with ethyl acetate
  4. washThe organic layer was washed with 1 mol/L hydrochloric acid
  5. dry with materiala saturated aqueous sodium hydrogen carbonate solution, and saturated brine successively, dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (eluting solvent: methanol-dichloromethane)

Sources & evidence

ORD record
ord-3f0104466cfd40aa914c715b35d60211
Source dataset
uspto-grants-2014_08
Patent number
US08815903B2

Reaction notes

Loading…