Dichloromethane → HCID 68674364、化合物

HRID 1183091ノート

反応式

HRID 1183091 の反応式
C(P(CCCC)CCCC)CCC.C1COCC1.[OH:19][C:20]1[CH:39]=[CH:38][C:23]2[N:24]([CH2:34][CH:35]([CH3:37])[CH3:36])[C:25](=[O:33])[C:26]([CH3:32])([CH3:31])[C:27](=[O:30])[N:28]([CH3:29])[C:22]=2[CH:21]=1.[N:40]1[CH:45]=[CH:44][CH:43]=[C:42]([CH2:46][CH2:47][N:48]([CH2:53][C:54]2[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=2)[CH2:49][CH2:50][CH2:51]O)[CH:41]=1.[Cl:60]CCl>O>[ClH:60].[ClH:60].[ClH:60].[CH2:34]([N:24]1[C:25](=[O:33])[C:26]([CH3:31])([CH3:32])[C:27](=[O:30])[N:28]([CH3:29])[C:22]2[CH:21]=[C:20]([O:19][CH2:51][CH2:50][CH2:49][N:48]([CH2:47][CH2:46][C:42]3[CH:41]=[N:40][CH:45]=[CH:44][CH:43]=3)[CH2:53][C:54]3[CH:59]=[CH:58][N:57]=[CH:56][CH:55]=3)[CH:39]=[CH:38][C:23]1=2)[CH:35]([CH3:36])[CH3:37]

参加物

7

反応物 5

HCID 6344DichloromethaneHCID 8028TetrahydrofuranHCID 13831TributylphosphineHCID 50943225HCID 50943225、化合物HCID 669609373-[(2-Pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol

生成物 1

HCID 68674364HCID 68674364、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

N,N,N′,N′-Tetramethylazodicarboxamide(TMAD) (189 mg, 1.1 mmol) and tri-n-butyl phosphine (0.28 ml, 1.1 mmol) were added to a THF solution (5 ml) of 7-hydroxy-1-isobutyl-3,3,5-trimethyl-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione (213 mg, 0.73 mmol) and 3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propan-1-ol (199 mg, 0.73 mmol), and stirred at room temperature overnight. Water was added to the reaction mixture, 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 (ethyl acetate:methanol=20:1→10:1). The purified product was concentrated under reduced pressure, and the residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1→10:1) again. The purified product was concentrated under reduced pressure. A 4N-hydrogen chloride ethyl acetate solution (0.57 ml) was added to the residue (ethyl acetate solution), stirred at room temperature for 30 minutes, and concentrated to dryness under reduced pressure to thereby obtain 480 mg (yield: quantitative) of 1-isobutyl-3,3,5-trimethyl-7-{3-[(2-pyridin-3-ylethyl)pyridin-4-ylmethylamino]propoxy}-1,5-dihydrobenzo[b][1,4]diazepine-2,4-dione trihydrochloride as a white amorphous solid.

後処理

  1. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (ethyl acetate:methanol=20:1→10:1)
  4. concentrationThe purified product was concentrated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (dichloromethane:methanol=40:1→10:1) again
  6. concentrationThe purified product was concentrated under reduced pressure
  7. additionA 4N-hydrogen chloride ethyl acetate solution (0.57 ml) was added to the residue (ethyl acetate solution)
  8. stirringstirred at room temperature for 30 minutes
  9. concentrationconcentrated to dryness under reduced pressure

出典と根拠

ORDレコード
ord-7ca4db89fc8d4652826d385f430520f5
出典データセット
uspto-grants-2014_03
特許番号
US08664217B2

反応ノート

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