Pyridine → 3H-1,5-Benzodiazepine, 2,4-bis(4-methyl-1-piperazinyl)-3-propylidene-

HRID 1782398ノート

反応式

HRID 1782398 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]([CH:26](O)[CH2:27][CH3:28])[C:10]([N:19]3[CH2:24][CH2:23][N:22]([CH3:25])[CH2:21][CH2:20]3)=[N:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:4][CH2:3]1.C(N(CC)CC)C.N1C=CC=CC=1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.[OH-].[Na+]>O1CCCC1.ClCCl.CO>[CH3:1][N:2]1[CH2:3][CH2:4][N:5]([C:8]2[C:9](=[CH:26][CH2:27][CH3:28])[C:10]([N:19]3[CH2:20][CH2:21][N:22]([CH3:25])[CH2:23][CH2:24]3)=[N:11][C:12]3[CH:18]=[CH:17][CH:16]=[CH:15][C:13]=3[N:14]=2)[CH2:6][CH2:7]1

参加物

9

反応物 5

HCID 1049PyridineHCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 14798Sodium HydroxideHCID 100238171-[2,4-bis (4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepin-3-yl]-1-propanol

生成物 1

HCID 102492283H-1,5-Benzodiazepine, 2,4-bis(4-methyl-1-piperazinyl)-3-propylidene-収率 85.1%

試薬・触媒・溶媒 3

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
0 °C

実験手順

To a suspension of 1-[2,4-bis(4-methyl-1-piperazinyl)-3H-[1,5]benzodiazepin-3-yl]-1-propanol (1.195 g, 3 mmol), triethylamine (2.50 ml, 18 mmol) and pyridine (0.024 ml, 0.3 mmol) in tetrahydrofuran (10 ml) under constant flow of argon, at 0° C., a solution of trifluoroacetic anhydride (1.26 ml, 9 mmol) in tetrahydrofuran (5 ml) was added dropwise. The reaction mixture was stirred for another hour at 0° C. Methanol (5 ml) was added. The solution was allowed to warm to 10° C., while strongly agitated NaOH (1 M, 20 ml) was added dropwise. Dichloromethane (30 ml) was added and the phases were separated. The organic phase was dried over anhydrous Na2SO4 and the solvent was evaporated at reduced pressure. The crude product was suspended in isopropyl ether (8 ml) and filtered off. The filtrate was evaporated at reduced pressure to give 0.971 g (84%) of the title compound as a yellow resin. The product obtained was characterized using 1H-NMR spectroscopy and was found to be identical to the product obtained by method A.

後処理

  1. additionwas added dropwise
  2. customthe phases were separated
  3. dry with materialThe organic phase was dried over anhydrous Na2SO4
  4. customthe solvent was evaporated at reduced pressure
  5. filtrationfiltered off
  6. customThe filtrate was evaporated at reduced pressure

出典と根拠

ORDレコード
ord-543564be2c4b452e9aa1c6dde5f5860e
出典データセット
uspto-grants-2009_03
特許番号
US07498433B2

反応ノート

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