Sodium Methoxide → 4-[2-(2,2-Dimethyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-1,3-thiazol-4-yl]benzonitrile

HRID 1436431Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1436431
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[N:10]=[C:11]([NH:14][C:15]([CH3:23])([CH3:22])/[CH:16]=[CH:17]/[C:18](OC)=[O:19])[S:12][CH:13]=2)=[CH:5][CH:4]=1)#[N:2].C[O-].[Na+]>O1CCCC1>[CH3:22][C:15]1([CH3:23])[CH:16]=[CH:17][C:18](=[O:19])[N:14]1[C:11]1[S:12][CH:13]=[C:9]([C:6]2[CH:7]=[CH:8][C:3]([C:1]#[N:2])=[CH:4][CH:5]=2)[N:10]=1

Komponenten

4

Edukt 2

HCID 10942334Sodium MethoxideHCID 86618612Methyl (2E)-4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpent-2-enoate

Produkt 1

HCID 247386264-[2-(2,2-Dimethyl-5-oxo-2,5-dihydro-1H-pyrrol-1-yl)-1,3-thiazol-4-yl]benzonitrileAusbeute 78 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Methyl (2E)-4-{[4-(4-cyanophenyl)-1,3-thiazol-2-yl]amino}-4-methylpent-2-enoate (0.15 g, 0.46 mmol), prepared in the previous step, was dissolved in tetrahydrofuran (2 mL) and sodium methoxide (53 mg, 1.0 mmol) was added. The mixture was stirred for 2 h, quenched with saturated NH4Cl, diluted with ethyl acetate, washed with H2O, brine, dried over anhydrous MgSO4, filtered and concentrated. Flash chromatography (20% acetone/hexane) afforded the title compound (0.105 g, 78%) as a white solid. HRMS: calcd for C16H13N3OS+H+, 296.08521; found (ESI, [M+H]+), 296.0867; Analytical HPLC: purity 99.0% at 210-370 nm, 9.8 min; 97.8% at 304 nm, 9.8 min; the Xterra® RP18 column, 3.5μ, 150×4.6 mm column, 1.2 mL/min, 85/15-5/95 (Ammon. Form. Buff. pH=3.5/ACN+MeOH) for 10 min, hold 4 min.

Aufarbeitung

  1. customquenched with saturated NH4Cl
  2. additiondiluted with ethyl acetate
  3. washwashed with H2O, brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-74801089bb2b4f53b85f4bda22796707
Quelldatensatz
uspto-grants-2009_11
Patentnummer
US07618990B2

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