Water → HCID 68109186, compound

HRID 2174638Notes

Reaction equation

HRID 2174638 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[C:3]([C:11]2[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=3[NH:15][CH2:14][CH2:13][N:12]=2)[CH:2]=1.[CH:22](I)([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[CH:22]([N:15]1[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[C:11]([C:3]2[CH:2]=[N:1][C:10]3[C:5]([CH:4]=2)=[CH:6][CH:7]=[CH:8][CH:9]=3)=[N:12][CH2:13][CH2:14]1)([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6362Isopropyl iodide2×HCID 11430Potassium Carbonate2×HCID 67067110HCID 67067110, compound

Product 1

HCID 68109186HCID 68109186, compoundYield 8.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

2,3-Dihydro-5-(3-quinolinyl)-1H-1,4-benzodiazepine (0.12 g, 0.44 mmol) was dissolved in 5 mL of dimethyl formamide, and added with isopropyl iodide (0.11 g, 0.65 mmol) and potassium carbonate (0.10 g, 0.72 mmol), followed by stirring at 100° C. for 48 hours. Isopropyl iodide (0.22 g, 1.29 mmol) and potassium carbonate (0.20 g, 1.45 mmol) were added to the resulting reaction solution, followed by stirring at 100° C. for 14 hours. The resulting reaction solution was cooled to room temperature, and cold water was poured into the reaction solution, followed by extracting with ethyl acetate. The organic layer was washed with brine, followed by drying magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (chloroform:ethyl acetate=7:3) to obtain the target compound (0.012 g, yield: 8.7%).

Workup

  1. stirringby stirring at 100° C. for 14 hours
  2. customThe resulting reaction solution
  3. temperaturewas cooled to room temperature
  4. extractionby extracting with ethyl acetate
  5. washThe organic layer was washed with brine
  6. dry with materialby drying magnesium sulfate
  7. distillationThe solvent was distilled off under reduced pressure
  8. customThe resulting residue was purified by silica gel column chromatography (chloroform:ethyl acetate=7:3)

Sources & evidence

ORD record
ord-e51a8d71ba9741808ab13f1456c5d4c7
Source dataset
uspto-grants-2015_06
Patent number
US09062024B2

Reaction notes

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