Reaktion #1974531

Reaktionsgleichung

2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid

N,N-diisopropylethylamine

N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide

1-hydroxybenzotriazole

benzo[b]thiophen-2-ylmethanamine

→

title compound

Ausbeute 78.0%

N-(Benzo[b]thiophen-2-ylmethyl)-2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxamide

Ausbeute 78.0%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe reaction mixture was stirred at ambient temperature for 24 hours
2. 2
   SonstigeThe solvent was removed in vacuo
3. 3
   workup.DISSOLUTIONthe residue was dissolved in dichloromethane (50 mL)
4. 4
   Waschenwashed with saturated aqueous sodium bicarbonate (2×5 mL) and brine (10 mL)
5. 5
   TrocknenThe organic layer was dried over anhydrous sodium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated in vacuo
8. 8
   SonstigeThe residue was recrystallized from ethyl acetate and hexane
9. 9
   FiltrationThe solid was collected by filtration
10. 10
    Waschenwashed with methanol and hexane

Vorschrift

To a solution of 2-(4-(benzyloxy)-2-oxopyridin-1(2H)-yl)-4-methylthiazole-5-carboxylic acid (0.20 g, 0.58 mmol) in anhydrous N,N-dimethylformamide (10 mL) was added N,N-diisopropylethylamine (0.27 g, 2.10 mmol) and N-(3-dimethylaminopropyl)-N′-ethylcarbodiimide (0.18 g, 0.93 mmol). The mixture was stirred for 30 minutes, followed by the addition of 1-hydroxybenzotriazole (0.11 g, 0.81 mmol) and benzo[b]thiophen-2-ylmethanamine (0.14 mL, 0.87 mmol). The reaction mixture was stirred at ambient temperature for 24 hours. The solvent was removed in vacuo and the residue was dissolved in dichloromethane (50 mL), washed with saturated aqueous sodium bicarbonate (2×5 mL) and brine (10 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was recrystallized from ethyl acetate and hexane. The solid was collected by filtration and washed with methanol and hexane. The title compound was obtained as a colorless solid in 78% yield (0.22 g): 1H NMR (300 MHz, DMSO-d6) δ 8.98 (t, J=5.8 Hz, 1H), 8.61 (d, J=8.1 Hz, 1H), 7.82-7.85 (m, 1H), 7.76-7.73 (m, 1H), 7.51-7.23 (m, 8H), 6.34 (dd, J=8.1, 2.7 Hz, 1H), 6.23 (d, J=2.7 Hz, 1H), 5.16 (s, 2H), 4.65-4.63 (m, 2H), 2.56 (s, 3H); MS (ES+) m/z 488.1 (M+1).

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