1,2-Dichloroethane → HCID 67002193, compound

Participants

Reaction Steps

In a round-bottomed flask were combined 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid (150 mg, 0.45 mmol), 2-(1-amino-cyclopentyl)-propan-2-ol hydrochloride (115 mg, 0.64 mmol), EDC (95 mg, 0.50 mmol), and HOBt (67 mg, 0.50 mmol). Then added DMF (2 mL) followed by i-Pr2NEt (0.20 mL, 1.12 mmol). The reaction mixture was stirred at room temperature overnight then quenched with H2O and extracted with EtOAc (3×). The combined organics were washed with H2O (3×) and brine then dried over Na2SO4 and concentrated. The residue was purified by chromatography over 12 g of SiO2 using EtOAc/hexanes (gradient: 0-30% EtOAc) to afford 209 mg (96%) of 2-cyclopropyl-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazine-7-carboxylic acid [1-(1-hydroxy-1-methyl-ethyl)-cyclopentyl]-amide as a pale yellow oil.

Provenance & Evidence