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

HRID 1744065Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1744065
[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]

Komponenten

8

Edukt 2

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

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]−.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-2827916379644f8db9cb0d09958ef59a
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07012075B2

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