2-(Pyridin-3-yl)ethan-1-amine → 1-Ethyl-3,3,5-trimethyl-7-[3-(2-pyridin-3-ylethylamino) propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 1183088Notes

Reaction equation

HRID 1183088 reaction equation
[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22]I)[CH:17]=[CH:18][C:4]1=2)[CH3:2].[NH2:24][CH2:25][CH2:26][C:27]1[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=1>CO>[CH2:1]([N:3]1[C:9](=[O:10])[C:8]([CH3:12])([CH3:11])[C:7](=[O:13])[N:6]([CH3:14])[C:5]2[CH:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][NH:24][CH2:25][CH2:26][C:27]3[CH:28]=[N:29][CH:30]=[CH:31][CH:32]=3)[CH:17]=[CH:18][C:4]1=2)[CH3:2]

Participants

4

Reactant 2

HCID 8540512-(Pyridin-3-yl)ethan-1-amineHCID 686727921-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Product 1

HCID 686730021-Ethyl-3,3,5-trimethyl-7-[3-(2-pyridin-3-ylethylamino) propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneYield 70%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

1-Ethyl-7-(3-iodopropoxy)-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (5.3 mmol) was added to a methanol solution (100 ml) of 3-(2-aminoethyl)pyridine (3.3 g, 26.7 mmol), and stirred at 50° C. for 9 hours. The reaction mixture was cooled to room temperature, and concentrated under reduced pressure. Water was added to the residue, and extraction with dichloromethane was performed. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1→10:1). The purified product was concentrated under reduced pressure, and the residue was purified by basic silica gel column chromatography (ethyl acetate:methanol=1:0→10:1) again. The purified product was concentrated under reduced pressure to thereby obtain 1.57 g (yield: 70%) of 1-ethyl-3,3,5-trimethyl-7-[3-(2-pyridin-3-ylethylamino)propoxy]-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a yellow oil.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under reduced pressure
  3. additionWater was added to the residue, and extraction with dichloromethane
  4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1→10:1)
  7. concentrationThe purified product was concentrated under reduced pressure
  8. customthe residue was purified by basic silica gel column chromatography (ethyl acetate:methanol=1:0→10:1) again
  9. concentrationThe purified product was concentrated under reduced pressure

Sources & evidence

ORD record
ord-b4f802e332bd45b186b93b8ae16129cb
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

Loading…