Diethyl Pyrocarbonate → 2-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]prop-2-enamide

HRID 1479803Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1479803
[CH2:1]([N:3]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4](=[CH2:8])[C:5]([OH:7])=O)[CH3:2].CCOC(OC(OCC)=O)=O.[F:30][C:31]([F:47])([F:46])[C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[C:42]([CH2:44][NH2:45])[CH:41]=[CH:40][N:39]=2)=[CH:34][CH:33]=1>C1COCC1>[CH2:1]([N:3]([S:9]([C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)(=[O:11])=[O:10])[C:4](=[CH2:8])[C:5]([NH:45][CH2:44][C:42]1[CH:41]=[CH:40][N:39]=[C:38]([C:35]2[CH:36]=[CH:37][C:32]([C:31]([F:47])([F:30])[F:46])=[CH:33][CH:34]=2)[CH:43]=1)=[O:7])[CH3:2]

Komponenten

5

Edukt 3

HCID 3051Diethyl PyrocarbonateHCID 68758847HCID 68758847, VerbindungHCID 903842012-[Ethyl-(4-fluorophenyl)sulfonyl-amino]prop-2-enoic acid

Produkt 1

HCID 783246012-[ethyl-(4-fluorophenyl)sulfonyl-amino]-N-[[2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methyl]prop-2-enamideAusbeute 19,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Acid 4B (273.28 mg, 1 mmol) was dissolved in 10 ml of THF and at rt DEPC (1.1 equiv, 0.15 ml) and [2-[4-(trifluoromethyl)phenyl]-4-pyridyl]methanamine 21A (1.1 equiv., 277.5 mg) were added to the solution. The mixture was stirred at rt overnight then evaporated. The residue was dissolved in AcOEt (30 ml) and washed with water (1×20 ml) and brine. The organic phase was dried over sodium sulfate and concentrated under vacuum. The purification of the crude by chromatographic column (EtOAc 1/petroleum ether 1) afforded 100 mg of a white solid. Yield=19% 1HNMR (DMSO, 400 MHz) δ 1.09 (3H, t, J=7.2 Hz), 3.39 (2H, q, J=6.8 Hz), 4.48 (2H, d, J=6 Hz), 5.15 (1H, s), 6.14 (1H, s), 7.36 (1H, dd, J=4.8 Hz, J′=1.2 Hz), 7.47 (2H, t, J=8.8 Hz), 7.84 (4H, m), 8.01 (1H, s), 8.30 (2H, d, J=8 Hz), 8.64 (1H, dd, J=5.2 Hz, J′=0.8 Hz), 8.89 (1H, bt) [M+1] 508.7 (C24H21F4N3O3S requires 507.50).

Aufarbeitung

  1. additionwere added to the solution
  2. customthen evaporated
  3. dissolutionThe residue was dissolved in AcOEt (30 ml)
  4. washwashed with water (1×20 ml) and brine
  5. dry with materialThe organic phase was dried over sodium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe purification of the crude by chromatographic column (EtOAc 1/petroleum ether 1)

Quellen und Nachweise

ORD-Eintrag
ord-6138cc1de4934b42858f387fb8a57c70
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409864B2

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