Sodium Hydroxide → HCID 86703987, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[1-methyl-4-(1-methyl piperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenylamine (example 173) (50 mg, 0.124 mmole) in ACN (1 mL) are added DIEA (65 μL, 0.372 mmole) and tertbutylisocyanate (21 μL, 0.182 mmole). The reaction mixture is heated overnight at 80° C. Water is added as well as 1N NaOH to pH 10. The aqueous phase is extracted three times with CH2Cl2. The organic phase is dried over MgSO4, filtered, and the solvent is removed under reduced pressure. The residue is pre-purified by silica gel chromatography eluting with (CH2Cl2:MeOH:NH4OH) from (98:2:0.2) to (95:5:0.5), and the residue is submitted to a preparative TLC on silica gel eluting with (CH2Cl2:MeOH:NH4OH) from (9:1:1) to give 1-tert-butyl-3-{4-[1-methyl-4-(1-methylpiperidin-4-yloxy)-9,10-dihydro-4H-3,10a-diaza-benzo[f]azulen-2-yl]-phenyl}-urea melting at 173° C.

Provenance & Evidence