Methanol → 1-Ethyl-3,3,5-trimethyl-7-{3-[(pyridin-4-ylmethyl)amino]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione

HRID 2196084

反応式

HRID 2196084 の反応式
[N:1]1[CH:6]=[CH:5][C:4]([CH:7]=O)=[CH:3][CH:2]=1.CO.[NH2:11][CH2:12][CH2:13][CH2:14][O:15][C:16]1[CH:33]=[CH:32][C:19]2[N:20]([CH2:30][CH3:31])[C:21](=[O:29])[C:22]([CH3:28])([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]=2[CH:17]=1.[BH4-].[Na+]>C(OCC)(=O)C.O>[CH2:30]([N:20]1[C:21](=[O:29])[C:22]([CH3:28])([CH3:27])[C:23](=[O:26])[N:24]([CH3:25])[C:18]2[CH:17]=[C:16]([O:15][CH2:14][CH2:13][CH2:12][NH:11][CH2:7][C:4]3[CH:3]=[CH:2][N:1]=[CH:6][CH:5]=3)[CH:33]=[CH:32][C:19]1=2)[CH3:31]

参加物

7

反応物 4

HCID 887MethanolHCID 133894-PyridinecarboxaldehydeHCID 4311764Sodium borohydrideHCID 68673521HCID 68673521、化合物

生成物 1

HCID 686728021-Ethyl-3,3,5-trimethyl-7-{3-[(pyridin-4-ylmethyl)amino]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione収率 84.2%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

実験手順

4-Pyridinecarbaldehyde (0.64 ml, 6.8 mmol) was added to a methanol solution (10 ml) of 7-(3-aminopropoxy)-1-ethyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (2.18 g, 6.8 mmol), and stirred under a nitrogen atmosphere at room temperature for 1.5 hours. The reaction mixture was cooled in an ice water bath, and sodium borohydride (257 mg, 6.8 mmol) was added thereto at 0° C. The mixture was then 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 (ethyl acetate:methanol=9:1→3:2). The purified product was concentrated under reduced pressure to thereby obtain 2.35 g (yield: 84%) of 1-ethyl-3,3,5-trimethyl-7-{3-[(pyridin-4-ylmethyl)amino]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione as a pale yellow oil.

後処理

  1. temperatureThe reaction mixture was cooled in an ice water bath
  2. customat 0° C
  3. stirringThe mixture was then stirred at room temperature overnight
  4. washThe organic layer was washed with water
  5. dry with materiala saturated sodium chloride aqueous solution, in this order, dried over anhydrous magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=9:1→3:2)
  8. concentrationThe purified product was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-f117cbcccedf42c3a149dff2ea696f80
出典データセット
uspto-grants-2012_12
特許番号
US08338406B2

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