Sodium Hydroxide → HCID 178434339, compound

Participants

Reaction Conditions

Reaction Steps

A flask was charged with tert-butyl 3-methyl-6-(4-(3-tosyl-6,7-dihydro-3H-imidazo[4,5-c]pyridin-5 (4H)-yl)furo[3,2-d]pyrimidin-2-ylamino)-1H-indazole-1-carboxylate (0.040 g, 0.062 mmol, prepared using C from Preparation #AJ.1, A with 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] and B with Example #3, Step B) and 1,4-dioxane (1.0 mL). To the mixture was added 2 N aqueous NaOH, (0.094 mL, 0.19 mmol) and the mixture was heated to about 65° C. for about 4.5 h. The mixture was cooled to rt and DCM (10 mL) and saturated aqueous NH4Cl (3 mL) were added. The layers were separated and a solid remained in the aqueous layer. The solid was collected by vacuum filtration and dried overnight at about 60° C. in a vacuum oven to give 4-(6,7-dihydro-3H-imidazo[4,5-c]pyridin-5 (4H)-yl)-N-(3-methyl-1H-indazol-6-yl)furo[3,2-d]pyrimidin-2-amine (0.008 g, 33%): LC/MS (Table 2, Method c) Rt=1.60 min; MS m/z: 387 (M+H)+. Syk IC50=A

Provenance & Evidence