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

HRID 1782398노트

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HRID 1782398 반응식
[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

참가 물질

9

반응물 5

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

생성물 1

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

시약·촉매·용매 3

HCID 887Methanol용매HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-543564be2c4b452e9aa1c6dde5f5860e
출처 데이터셋
uspto-grants-2009_03
특허 번호
US07498433B2

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