1,2-Dichloroethane → 7-(3-{bis-[2-(1-oxo-1H-isoquinolin-2-yl)ethyl]amino}propoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 1183099Notes

Reaction equation

HRID 1183099 reaction equation
[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]1[CH2:12][CH:13]=O.Cl[CH2:16][CH2:17]Cl.[NH2:19][CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:41]=[CH:40][C:27]2[N:28]([CH2:38][CH3:39])[C:29](=[O:37])[C:30]([CH3:36])([CH3:35])[C:31](=[O:34])[N:32]([CH3:33])[C:26]=2[CH:25]=1.[Na]>C(OCC)(=O)C.O>[O:1]=[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[CH:5]=[CH:4][N:3]1[CH2:16][CH2:17][N:19]([CH2:13][CH2:12][N:3]1[CH:4]=[CH:5][C:6]2[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=2)[C:2]1=[O:1])[CH2:20][CH2:21][CH2:22][O:23][C:24]1[CH:41]=[CH:40][C:27]2[N:28]([CH2:38][CH3:39])[C:29](=[O:37])[C:30]([CH3:35])([CH3:36])[C:31](=[O:34])[N:32]([CH3:33])[C:26]=2[CH:25]=1

Participants

7

Reactant 4

HCID 111,2-DichloroethaneHCID 5360545SodiumHCID 686735217-(3-Aminopropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dioneHCID 81883460(1-Oxo-1H-isoquinolin-2-yl)acetaldehyde

Product 1

HCID 686734607-(3-{bis-[2-(1-oxo-1H-isoquinolin-2-yl)ethyl]amino}propoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

(1-Oxo-1H-isoquinolin-2-yl)acetaldehyde (207 mg, 1.1 mmol) was added to a 1,2-dichloroethane solution (4 ml) of 7-(3-aminopropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (329 mg, 1.0 mmol) and sodium triacetoxyhydroborate (381 mg, 1.8 mmol), and stirred at room temperature overnight. Water was added to the reaction mixture, and extraction with ethyl acetate was performed. The organic layer was washed with water, and a saturated sodium chloride aqueous solution, in this order, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1). The purified product was concentrated under reduced pressure to thereby obtain 7-(3-{bis-[2-(1-oxo-1H-isoquinolin-2-yl)ethyl]amino}propoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione.

Workup

  1. washThe organic layer was washed with water
  2. dry with materiala saturated sodium chloride aqueous solution, in this order, dried over anhydrous magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (dichloromethane:methanol=20:1)
  5. concentrationThe purified product was concentrated under reduced pressure to thereby obtain 7-(3-{bis-[2-(1-oxo-1H-isoquinolin-2-yl)ethyl]amino}propoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

Sources & evidence

ORD record
ord-c6ab8d45d47a442cb7d796987542b617
Source dataset
uspto-grants-2014_03
Patent number
US08664217B2

Reaction notes

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