benzyl N-[(4-methylpiperidin-4-yl)methyl]carbamate

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of tert-butyl 6-(4-(4-((benzyloxycarbonylamino)methyl)-4-methylpiperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-1H-indazole-1-carboxylate (0.13 g, 0.213 mmol, (prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] with benzyl (4-methylpiperidin-4-yl)methylcarbamate [U.S. Pat. No. 6,140,333 example 3 step 5]), B with tert-butyl 6-amino-1H-indazole-1-carboxylate [Frontier] and C) in AcOH (3 mL) was added HBr (1 mL). The mixture was stirred at about 40° C. for about 8 h. Water (30 mL) was added and the mixture was extracted with DCM (4×20 mL). The mixture was concentrated in vacuo to give 4-(4-(aminomethyl)-4-methylpiperidin-1-yl)-N-(1H-indazol-6-yl)furo[3,2-d]pyrimidin-2-amine (0.015 g, 19%): LC/MS (Table 2, Method h) Rt=1.72 min; MS m/z: 378 (M+H)+. Syk IC50=A (prepared the mixture was extracted with DCM (4×20 mL) The mixture was concentrated in vacuo

Conditions: temp:40.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a mixture of tert-butyl 6-(4-(4-((benzyloxycarbonylamino)methyl)-4-methylpiperidin-1-yl)furo[3,2-d]pyrimidin-2-ylamino)-1H-indazole-1-carboxylate (0.13 g, 0.213 mmol, (prepared using A from 2,4-dichlorofuro[3,2-d]pyrimidine [ArkPharm] with benzyl (4-methylpiperidin-4-yl)methylcarbamate [U.S. Pat. No. 6,140,333 example 3 step 5]), B with tert-butyl 6-amino-1H-indazole-1-carboxylate [Frontier] and C) in AcOH (3 mL) was added HBr (1 mL). The mixture was stirred at about 40° C. for about 8 h. Water (30 mL) was added and the mixture was extracted with DCM (4×20 mL). The mixture was concentrated in vacuo to give 4-(4-(aminomethyl)-4-methylpiperidin-1-yl)-N-(1H-indazol-6-yl)furo[3,2-d]pyrimidin-2-amine (0.015 g, 19%): LC/MS (Table 2, Method h) Rt=1.72 min; MS m/z: 378 (M+H)+. Syk IC50=A (prepared the mixture was extracted with DCM (4×20 mL) The mixture was concentrated in vacuo