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 1183099ノート

反応式

HRID 1183099 の反応式
[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

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-c6ab8d45d47a442cb7d796987542b617
出典データセット
uspto-grants-2014_03
特許番号
US08664217B2

反応ノート

読み込み中…