Diethyl Ether → HCID 86703993, compound

Participants

Reaction Steps

To a solution of 1,2-diiodo-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene (example 219) (437 mg, 1 mmole) in CH2Cl2 (4 mL) and THF (1 mL) at 0° C. is added EtMgBr 3M solution in Et2O (1 mL, 3 mmoles). The ice bath is removed and the reaction mixture is stirred at room temperature for 90 minutes. Tert-butylisocyanate (618 μL, 5 mmoles) is added to the above solution. The reaction mixture is stirred at room temperature for 3 hours. A (1:1) solution of saturated aqueous NH4Cl and concentrated NH4OH is added and the aqueous phase is extracted three times with CH2Cl2. The organic phase is dried over MgSO4, filtered and the solvent removed under reduced pressure. The residue is purified by silica gel chromatography eluting with (CH2Cl2:MeOH:NH4OH) (98:2:0.2) to (95:5:0.5). The residue is triturated in iPr2O to afford 1-methyl-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulene-2-carboxylic acid benzylamide melting at 161° C.

Provenance & Evidence