Pyridine → HCID 68109721, compound

HRID 2174637Notes

Reaction equation

HRID 2174637 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.[C:22](OC(=O)C)(=[O:24])[CH3:23].N1C=CC=CC=1.C(OCC)(=O)C>C(Cl)Cl>[C: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)(=[O:24])[CH3:23]

Participants

6

Reactant 4

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 8857Ethyl AcetateHCID 67067110HCID 67067110, compound

Product 1

HCID 68109721HCID 68109721, compoundYield 73.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-Dihydro-5-(3-quinolinyl)-1H-1,4-benzodiazepine (0.20 g, 0.73 mmol) was dissolved in 10 mL of methylene chloride, and acetic anhydride (0.1 mL, 1.1 mmol), pyridine (0.18 mL, 2.2 mmol) were added to the resulting solution, followed by stirring at room temperature for 2 hours. Then the resulting solution was distilled off under redused pressure for 14 hours. The resulting reaction solution was cooled to room temperature and added with ethyl acetate. Then the solution was washed with 0.5N citric acid solution, brine and saturated bicarbonate water, followed by drying with magnesium sulfate. The solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=9:1) to obtain the target compound (0.17 g, yield: 15%).

Workup

  1. distillationThen the resulting solution was distilled off under redused pressure for 14 hours
  2. customThe resulting reaction solution
  3. temperaturewas cooled to room temperature
  4. washThen the solution was washed with 0.5N citric acid solution, brine and saturated bicarbonate water
  5. dry with materialby drying with magnesium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customThe resulting residue was purified by silica gel column chromatography (eluent: chloroform:methanol=9:1)

Sources & evidence

ORD record
ord-d39f55476f444fd89d54523f2f14fac6
Source dataset
uspto-grants-2015_06
Patent number
US09062024B2

Reaction notes

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