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Triethylamine → 2-Oxo-1-phenyl-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

HRID 1767541
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1767541
C(N(CC)CC)C.[C:8]1(B(O)O)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[O:17]=[C:18]1[C:27]([C:28]#[N:29])=[C:26]([N:30]2[CH2:35][CH2:34][N:33]([C:36]([C:38]3[S:39][CH:40]=[CH:41][CH:42]=3)=[O:37])[CH2:32][CH2:31]2)[C:25]2[C:20](=[CH:21][CH:22]=[CH:23][CH:24]=2)[NH:19]1>ClCCl>[O:17]=[C:18]1[C:27]([C:28]#[N:29])=[C:26]([N:30]2[CH2:35][CH2:34][N:33]([C:36]([C:38]3[S:39][CH:40]=[CH:41][CH:42]=3)=[O:37])[CH2:32][CH2:31]2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[N:19]1[C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 66827Phenylboronic AcidHCID 210819432-Oxo-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrile

Produkt 1

HCID 210819392-Oxo-1-phenyl-4-[4-(thiophene-2-carbonyl)-piperazin-1-yl]-1,2-dihydro-quinolin-3-carbonitrileAusbeute 31 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344
Dichloromethane
Lösungsmittel

Versuchsvorschrift

Cupric acetate (497 mg, 2.74 mmol), triethylamine (380 μL, 2.74 mmol), and phenyl boronic acid (335 mg, 2.74 mmol) were added successively to a solution of Compound 116 (500 mg, 1.37 mmol) in dichloromethane. The solution was stirred at room temperature for 48 h. The solution was filtered through celite and washed successively by saturated NaHCO3 solution, water, and brine. The organic phase was dried over Na2SO4 and evaporated to yield a residue which was purified by flash chromatography eluting with 0–1% MeOH in dichloromethane gradient to get 187 mg (31%) of white solids. M.P. 289° C. 1H NMR (DMSO-d6): δ 3.78 (m, 4H), 4.02 (m, 4H), 6.60 (d, J=7.6 Hz, 1H), 7.22 (m, 1H), 7.38 (m, 3H), 7.57–7.71 (m, 5H), 7.88 (dd, J=0.8, 4.8 Hz, 1H), 8.02 (d, J=7.2 Hz, 1h). EIMS m/z 441 (M+1). Anal. (C25H20N4O2S) C, H, N.

Aufarbeitung

  1. filtrationThe solution was filtered through celite
  2. washwashed successively by saturated NaHCO3 solution, water, and brine
  3. dry with materialThe organic phase was dried over Na2SO4
  4. customevaporated
  5. customto yield a residue which
  6. customwas purified by flash chromatography
  7. washeluting with 0–1% MeOH in dichloromethane gradient

Quellen und Nachweise

ORD-Eintrag
ord-81a16668cd934323b7775c0a398daf4c
Quelldatensatz
uspto-grants-2007_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07235546B2

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