Water → N-{4-methyl-5-[5-(morpholin-4-ylsulfonyl)-3-thienyl]-1,3-thiazol-2-yl}acetamide

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Reaktionsgleichung

Br[C:2]1[S:3][C:4]([S:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)(=[O:19])=[O:18])=[CH:5][C:6]=1[C:7]1[S:11][C:10]([NH:12][C:13](=[O:15])[CH3:14])=[N:9][C:8]=1[CH3:16].C([Li])CCC.O>C1COCC1>[CH3:16][C:8]1[N:9]=[C:10]([NH:12][C:13](=[O:15])[CH3:14])[S:11][C:7]=1[C:6]1[CH:5]=[C:4]([S:17]([N:20]2[CH2:25][CH2:24][O:23][CH2:22][CH2:21]2)(=[O:19])=[O:18])[S:3][CH:2]=1

Komponenten

Reaktionsbedingungen

Temperatur: -70 °C

Versuchsvorschrift

N-{ 5-[2-bromo-5-(morpholin-4-ylsulfonyl)-3-thienyl]-4-methyl-1,3-thiazol-2-yl}acetamide (54 mg; 0.12 mmol; 1 eq) is dissolved in dry THF (5 ml) at −70° C. under an inert atmosphere. n-Butyllithium (0.16 ml; 1.6 M; 0.26 mmol; 2.20 eq) is added slowly and reaction stirred at −70° C. for 25 minutes before being hydrolyzed with water (0.3 ml). Crude material is warmed up to room temperature before being concentrated to dryness. Residue is then taken up with water (2 ml) and EtOAc (10 ml). The organic phases are decanted, dried over MgSO4, filtrated and evaporated. Crude material is purified by flash chromatography on silica gel using cyclohexane/EtOAc (10/90) as eluent, affording expected Compound (46) as an oil (30 mg; 67%).

Aufarbeitung

customreaction
temperatureCrude material is warmed up to room temperature
concentrationbefore being concentrated to dryness
customThe organic phases are decanted
dry with materialdried over MgSO4
filtrationfiltrated
customevaporated
customCrude material is purified by flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag: ord-40f5067d4a6b4a18901b170a2a092ed6
Quelldatensatz: uspto-grants-2011_02
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US07879888B2

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