bis[(2-methylpropan-2-yl)oxycarbonyl] carbonate

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

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

Procedure: To a solution of di-tert-butyl tricarbonate, (0.681 g, 2.595 mmol), in dry DCM (1 ml) was added a solution of D2, (0.5 g, 2.162 mmol) in dry DCM (1 ml) in one portion. After the initial effervescence, the solution was stirred at room temperature for 0.3 h. A solution of 5-aminoisoquinoline, (0.312 g, 2.162 mmol) in dry DCM (1 ml) was added. The reaction mixture was stirred at room temperature overnight. The resultant precipitate was removed by centrifugation, and the solid washed with ether and dried to give the title compound as a white solid. The reaction mixture was stirred at room temperature overnight The resultant precipitate was removed by centrifugation the solid washed with ether dried

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

Procedure: To a solution of di-tert-butyl tricarbonate (60 mg, 0.23 mmol) in DCM (1 ml) was added in one portion, a solution of 7-aminoquinoline (D55) (30 mg, 0.21 mmol) in DCM (1 ml). After 5 mins, when gas evolution was complete, tris -amine resin (12 mg 0.04 mmol) was added, then after 1 h a solution of 4-phenylpiperazine (32 ul, 0.21 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was then purified directly by SPE column chromatography, eluting with an EtOAc/60-80° C.-petroleum ether gradient, followed by treatment with excess methyl isocyanate resin to remove unreacted 7-aminoquinoline starting material from the product. On completion the resin was removed by filtration and filtrate concentrated in vacuo to give the title compound as an orange gum. 1H NMR (250 MHz, CDCl3) δ (ppm): 8.85 (dd, 1H), 8.09 (dd, 1H), 7.93 (dd, 1H), 7.82 (s, 1H), 7.76 (d, 1H), 7.30 (m, 3H), 6.94 (m, 3H), 6.83 (br, 1H), 3.72 (m, 4H), 3.28 (m, 4H). The reaction mixture was then purified directly by SPE column chromatography eluting with an EtOAc/60-80° C.-petroleum ether gradient to remove unreacted 7-aminoquinoline starting material from the product On completion the resin was removed by filtration and filtrate concentrated in vacuo

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

Procedure: To a solution of di-tert-butyl tricarbonate, (0.681 g, 2.595 mmol), in dry DCM (1 ml) was added a solution of D2, (0.5 g, 2.162 mmol) in dry DCM (1 ml) in one portion. After the initial effervescence, the solution was stirred at room temperature for 0.3 h. A solution of 5-aminoisoquinoline, (0.312 g, 2.162 mmol) in dry DCM (1 ml) was added. The reaction mixture was stirred at room temperature overnight. The resultant precipitate was removed by centrifugation, and the solid washed with ether and dried to give the title compound as a white solid. The reaction mixture was stirred at room temperature overnight The resultant precipitate was removed by centrifugation the solid washed with ether dried

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

Procedure: To a solution of di-tert-butyl tricarbonate (60 mg, 0.23 mmol) in DCM (1 ml) was added in one portion, a solution of 7-aminoquinoline (D55) (30 mg, 0.21 mmol) in DCM (1 ml). After 5 mins, when gas evolution was complete, tris -amine resin (12 mg 0.04 mmol) was added, then after 1 h a solution of 4-phenylpiperazine (32 ul, 0.21 mmol) was added and the reaction stirred at room temperature overnight. The reaction mixture was then purified directly by SPE column chromatography, eluting with an EtOAc/60-80° C.-petroleum ether gradient, followed by treatment with excess methyl isocyanate resin to remove unreacted 7-aminoquinoline starting material from the product. On completion the resin was removed by filtration and filtrate concentrated in vacuo to give the title compound as an orange gum. 1H NMR (250 MHz, CDCl3) δ (ppm): 8.85 (dd, 1H), 8.09 (dd, 1H), 7.93 (dd, 1H), 7.82 (s, 1H), 7.76 (d, 1H), 7.30 (m, 3H), 6.94 (m, 3H), 6.83 (br, 1H), 3.72 (m, 4H), 3.28 (m, 4H). The reaction mixture was then purified directly by SPE column chromatography eluting with an EtOAc/60-80° C.-petroleum ether gradient to remove unreacted 7-aminoquinoline starting material from the product On completion the resin was removed by filtration and filtrate concentrated in vacuo