Hydrochloric Acid → HCID 68658284, compound

HRID 1020664Notes

Reaction equation

HRID 1020664 reaction equation
[OH-].[Na+].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][N:14]([C:17]2[CH:25]=[C:24]3[C:20]([C:21]4[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][C:22]=4[N:23]3S(C3C=CC(C)=CC=3)(=O)=O)=[CH:19][CH:18]=2)[C:13](=[O:41])[CH:12]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[ClH:42].CCOCC>C(Cl)Cl.CO>[ClH:42].[CH2:3]([O:10][C:11]1[CH:16]=[CH:15][N:14]([C:17]2[CH:25]=[C:24]3[C:20]([C:21]4[CH2:39][CH2:38][N:37]([CH3:40])[CH2:36][C:22]=4[NH:23]3)=[CH:19][CH:18]=2)[C:13](=[O:41])[CH:12]=1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 3283Diethyl EtherHCID 14798Sodium HydroxideHCID 57950326HCID 57950326, compound

Product 1

HCID 68658284HCID 68658284, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent2×

Procedure

NaOH (644 mg, 16.1 mmol) was added to a solution of the 4-(benzyloxy)-1-(2-methyl-9-tosyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indol-7-yl)pyridin-2(1H)-one (174 mg, 0.322 mmol) in CH2Cl2/MeOH (10 mL) that had been degassed with N2. The resulting solution was heated at reflux with stirring for 2 h under N2. The solution was allowed to cool, saturated NH4Cl solution and CH2Cl2 were added, and the phases were separated. The organic phase was washed with saturated NaHCO3 solution, dried over Na2SO4 and concentrated under reduced pressure to yield a white solid. 1 M HCl in Et2O (0.38 ml, 0.38 mmol) was added to a solution of the white solid in 9:1 CH2Cl2/MeOH (10 mL) under N2, and the resulting solution was stirred at 25° C. for 30 min. The solution was concentrated, and the residue was diluted with a small amount of CH2Cl2/CH3CN. The resulting suspension was filtered, and the solid was dried under reduced pressure to yield the title compound (46 mg, 34%) as a white solid: mp 168-170° C.; 1H NMR (500 MHz, DMSO-d6) δ 11.30 (s, 1H), 10.50-10.41 (m, 1H), 7.58-7.52 (m, 2H), 7.49-7.40 (m, 4H), 7.39-7.35 (m, 2H), 6.96 (br d, J=8.0 Hz, 1H), 6.09 (br d, J=7.5 Hz, 1H), 5.97 (br s, 1H), 5.15 (s, 2H), 4.60 (br d, J=15.0 Hz, 1H), 4.41 (dd, J=15.0, 7.5 Hz, 1H), 3.78-3.71 (m, 1H), 3.45-3.38 (m, 1H), 3.09-2.98 (m, 5H); ESI MS m/z 386 [M+H]+.

Workup

  1. customhad been degassed with N2
  2. temperatureThe resulting solution was heated
  3. temperatureat reflux
  4. temperatureto cool
  5. additionsaturated NH4Cl solution and CH2Cl2 were added
  6. customthe phases were separated
  7. washThe organic phase was washed with saturated NaHCO3 solution
  8. dry with materialdried over Na2SO4
  9. concentrationconcentrated under reduced pressure
  10. customto yield a white solid
  11. stirringthe resulting solution was stirred at 25° C. for 30 min
  12. concentrationThe solution was concentrated
  13. additionthe residue was diluted with a small amount of CH2Cl2/CH3CN
  14. filtrationThe resulting suspension was filtered
  15. customthe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-6a27d1e45cb041a18c267e5b27d754a4
Source dataset
uspto-grants-2014_05
Patent number
US08716308B2

Reaction notes

Loading…