Diisopropylethylamine → HCID 178422074, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-{4-[1-methyl-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenylsulfanyl}-ethylamine (example 161) (170 mg, 0.368 mmole) in ACN (5 mL) are added N,N′-bis(tert-butoxycarbonyl)-1H-pyrazole-1-carboxamidine) (125 mg, 0.405 mmole) and DIEA (80 μL, 0.423 mmole). The reaction mixture is heated at 50° C. for 24 hours, then it is diluted with water and AcOEt. The organic phase is dried over MgSO4, filtered and the solvent is removed under reduced pressure. The residue is dissolved in CH2Cl2 (2 mL) and TFA is added (2 mL). The reaction mixture is stirred at room temperature for 3 hours. The reaction mixture is diluted with water, then 10N NaOH is added dropwise until pH 10 is reached. The aqueous phase is extracted three times with CH2Cl2. The organic phase dried over magnesium sulphate, filtered and the solvent is removed under reduced pressure. The residue is purified by silica gel chromatography using (CH2Cl2:MeOH:NH4OH) (90:1:0.1) to (8:2:0.2) to give N-(2-{4-[1-methyl-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenylsulfanyl}-ethyl)-guanidine.

Provenance & Evidence