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ChemicalBook CAS DataBase List 1H-Thieno[3,4-d]iMidazole-4-pentanaMide, hexahydro-2-oxo-N-2-propynyl-, (3aS,4S,6aR)-

1H-Thieno[3,4-d]iMidazole-4-pentanaMide, hexahydro-2-oxo-N-2-propynyl-, (3aS,4S,6aR)- synthesis

4synthesis methods
-

Yield:773888-45-2 98%

Reaction Conditions:

with triethylamine in tetrahydrofuran at 20; for 18 h;

Steps:

XVII.b b. Preparation of intermediate 62

Compound 60 (850 mg, 2.49 mmol, 1.0 eq.) was solubilized in dry dimethylformamide (20 ml_). After triethylamine (756 mg, 7.47 mmol, 1.0 nriL, 3.0 eq.) and propargylamine 61 (274 mg, 4.98 mmol, 0.3 ml_, 2.0 eq.) addition, reaction mixture was stirred at room temperature for 18h. Solvents were evaporated under vacuum and the residue was purified by flash chromatography [Biotage ; column AIT 40g; eluant: Cyclohexane / EtOAc; gradient: 100/0 · 100/0 (3 CV), 100/0 · 0/100 (12CV) and then 0/100 -> 0/100 (3CV)]. A second elution was done [CH2CI2 / MeOH; gradient: (3CV)], affording compound 62 (690 mg, yield 98%) as a ligh brown solid.

References:

WO2019/243273,2019,A1 Location in patent:Page/Page column 98-99

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