Tetrabutylammonium Fluoride → N-(cyanomethyl)-4-methyl-2-{[4'-(1-piperazinyl)[1,1'-biphenyl]-3-yl]oxy}pentanamide

HRID 1744065노트

반응식

HRID 1744065 반응식
[C:1]([CH2:3][NH:4][C:5]([CH:7]([O:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:24]=[CH:23][C:22]([N:25]3[CH2:30][CH2:29][N:28](C(O[Si](C(C)C)(C(C)C)C(C)C)=O)[CH2:27][CH2:26]3)=[CH:21][CH:20]=2)[CH:16]=[CH:17][CH:18]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])=[O:6])#[N:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1.C(OCC)C.C(OCC)(=O)C.O.C(=O)(O)[O-].[Na+]>[C:1]([CH2:3][NH:4][C:5](=[O:6])[CH:7]([O:12][C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[CH:21][C:22]([N:25]3[CH2:26][CH2:27][NH:28][CH2:29][CH2:30]3)=[CH:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1)[CH2:8][CH:9]([CH3:11])[CH3:10])#[N:2]

참가 물질

8

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 10282346Triisopropylsilyl 4-[3'-(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)[1,1'-biphenyl]-4-yl]-1-piperazinecarboxylate

생성물 1

HCID 10272735N-(cyanomethyl)-4-methyl-2-{[4'-(1-piperazinyl)[1,1'-biphenyl]-3-yl]oxy}pentanamide

시약·촉매·용매 5

HCID 962Water용매HCID 3283Diethyl Ether용매HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매HCID 516892Sodium Bicarbonate용매

실험 절차

Triisopropylsilyl 4-[3′-(1-{[(cyanomethyl)amino]carbonyl}-3-methylbutoxy)[1,1′-biphenyl]-4-yl]-1-piperazinecarboxylate (365 mg, 0.6 mmoles) in 8 mL of tetrahydrofuran was treated with tetrabutylammonium fluoride (0.75 mL, 1 M in THF, 0.75 mmoles) at 0° C. until the disappearance of the starting material was observed by TLC. The reaction was diluted with diethyl ether, ethyl acetate, water and sat. aq. sodium bicarbonate. The phases were separated, the organic phase washed with brine and dried over sodium sulfate. After concentration under reduced pressure, the residue was purified by flash chromatography (1% sat. aqueous ammonium hydroxide, 9% methanol, 90% dichloromethane) to afford N-(cyanomethyl)-4-methyl-2-{[4′-(1-piperazinyl)[1,1′-biphenyl]-3-yl]oxy}pentanamide. MS (−ESI): 405.3 [M−1]−.

후처리

  1. customThe phases were separated
  2. washthe organic phase washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationAfter concentration under reduced pressure
  5. customthe residue was purified by flash chromatography (1% sat. aqueous ammonium hydroxide, 9% methanol, 90% dichloromethane)

출처 및 근거

ORD 기록
ord-2827916379644f8db9cb0d09958ef59a
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07012075B2

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