Diethyl Pyrocarbonate → HCID 78320219, Verbindung

HRID 1479823Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1479823
[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([CH2:34][CH3:35])[C:11](=[CH2:33])[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]3[CH:27]=[CH:26][C:25](OC(F)(F)F)=[CH:24][CH:23]=3)[CH:17]=2)=[O:13])(=[O:9])=[O:8])=[CH:4][CH:3]=1.CCOC(OC(OCC)=O)=O.[F:47][C:48]([F:64])([F:63])C1C=CC(C2C=C(CN)C=CN=2)=CC=1>C1COCC1>[Cl:1][C:2]1[S:6][C:5]([S:7]([N:10]([CH2:34][CH3:35])[C:11](=[CH2:33])[C:12]([NH:14][CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[C:18]([C:22]3[CH:27]=[CH:26][C:25]([C:48]([F:64])([F:63])[F:47])=[CH:24][CH:23]=3)[CH:17]=2)=[O:13])(=[O:8])=[O:9])=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 3051Diethyl PyrocarbonateHCID 68758847HCID 68758847, VerbindungHCID 783199132-[(5-chloro-2-thienyl)sulfonyl-ethyl-amino]N-[[2-[4-(trifluoromethoxy)phenyl]-4-pyridyl]methyl]prop-2-enamide

Produkt 1

HCID 78320219HCID 78320219, VerbindungAusbeute 18,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Acid 7 (295.76 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 (1:1 EtOAc:petroleum ether) afforded 100 mg of a beige solid. Yield=18.8% 1HNMR (DMSO, 200 MHz) δ 1.12 (3H, t, J=7 Hz), 3.47 (2H, q), 4.48 (2H, d, J=6.4 Hz), 5.41 (1H, s), 6.25 (1H, s), 7.34 (2H, m), 7.59 (1H, d, J=4 Hz), 7.84 (2H, d, J=8 Hz), 7.98 (1H, bs), 8.28 (2H, d, J=8 Hz), 8.63 (1H, d, J=5 Hz), 8.91 (1H, bt) [M+1] 530.1 (C22H19ClF3N3O3S2 requires 529.98).

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 (1:1 EtOAc:petroleum ether)

Quellen und Nachweise

ORD-Eintrag
ord-25bfa1aab8fe419ca9a3d56db4f10fb7
Quelldatensatz
uspto-grants-2016_08
Patentnummer
US09409864B2

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