2-bromo-N-prop-2-ynylacetamide

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

Procedure: To a round bottom flask was added alkyne 18 (1.56 g, 8.84 mmol), 2-nitroimidazole 10 (1 g, 8.84 mmol) and K2CO3 (1.22 g, 8.84 mmol) in DMF (10 mL). The reaction was stirred overnight. The reaction was diluted with water (100 mL) and the resultant precipitate (1.2 g) was filtered off and washed with water (2×40 mL). The aqueous layer was extracted into EtOAc. The organic layer was concentrated to dryness and combined with the precipitate. The material was purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford a 19 white solid (324 mg, 18%). Mass Spec (lo-res): Calc'd for C8H8N4O3: 208.06; found: 209.10 (M+H). the resultant precipitate (1.2 g) was filtered off washed with water (2×40 mL) The aqueous layer was extracted into EtOAc The organic layer was concentrated to dryness The material was purified on a silica gel cartridge

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

Procedure: To a round bottom flask was added alkyne 18 (1.56 g, 8.84 mmol), 2-nitroimidazole 10 (1 g, 8.84 mmol) and K2CO3 (1.22 g, 8.84 mmol) in DMF (10 mL). The reaction was stirred overnight. The reaction was diluted with water (100 mL) and the resultant precipitate (1.2 g) was filtered off and washed with water (2×40 mL). The aqueous layer was extracted into EtOAc. The organic layer was concentrated to dryness and combined with the precipitate. The material was purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford a 19 white solid (324 mg, 18%). Mass Spec (lo-res): Calc'd for C8H8N4O3: 208.06; found: 209.10 (M+H). the resultant precipitate (1.2 g) was filtered off washed with water (2×40 mL) The aqueous layer was extracted into EtOAc The organic layer was concentrated to dryness The material was purified on a silica gel cartridge

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

Procedure: To a solution of 2-bromo-N-(prop-2-yn-1-yl)acetamide (0.7 g, 3.98 mmol) in DCM (10 mL) added N-methyl piperazine (0.66 mL, 5.96 mmol) drop wise. Reaction mixture stirred at rt for 16 h, diluted with DCM and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was triturated with ether-pentane, affording the title compound (0.38 g, 49%); LCMS: m/z=196.15 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 8.06 (d, J=6.1 Hz, 1H), 3.86 (dd, J=5.9, 2.5 Hz, 2H), 3.07 (t, J=2.5 Hz, 1H), 2.91 (s, 2H), 2.47-2.25 (m, 8H), 2.15 (s, 3H). Reaction mixture washed with water and brine The organic layer was dried over Na2SO4 concentrated in vacuo The crude residue was triturated with ether-pentane

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

Procedure: To a solution of 2-bromo-N-(prop-2-yn-1-yl)acetamide (0.6 g, 3.4 mmol) in acetonitrile (5 mL) was added trimethylamine (30% in MeOH, 5 mL). The mixture was stirred at room temperature for 16 h and concentrated in vacuo. The resulting residue was triturated with ether, resulting in the title compound (780 mg, 97%); LCMS: m/z=155.1 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 9.03 (t, J=5.3 Hz, 1H), 4.17 (s, 2H), 3.95 (dd, J=5.4, 2.6 Hz, 2H), 3.23 (s, 9H), 2.09 (s, 1H). concentrated in vacuo The resulting residue was triturated with ether

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

Procedure: To a round bottom flask was added alkyne 18 (1.56 g, 8.84 mmol), 2-nitroimidazole 10 (1 g, 8.84 mmol) and K2CO3 (1.22 g, 8.84 mmol) in DMF (10 mL). The reaction was stirred overnight. The reaction was diluted with water (100 mL) and the resultant precipitate (1.2 g) was filtered off and washed with water (2×40 mL). The aqueous layer was extracted into EtOAc. The organic layer was concentrated to dryness and combined with the precipitate. The material was purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford a 19 white solid (324 mg, 18%). Mass Spec (lo-res): Calc'd for C8H8N4O3: 208.06; found: 209.10 (M+H). the resultant precipitate (1.2 g) was filtered off washed with water (2×40 mL) The aqueous layer was extracted into EtOAc The organic layer was concentrated to dryness The material was purified on a silica gel cartridge

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

Procedure: To a round bottom flask was added alkyne 18 (1.56 g, 8.84 mmol), 2-nitroimidazole 10 (1 g, 8.84 mmol) and K2CO3 (1.22 g, 8.84 mmol) in DMF (10 mL). The reaction was stirred overnight. The reaction was diluted with water (100 mL) and the resultant precipitate (1.2 g) was filtered off and washed with water (2×40 mL). The aqueous layer was extracted into EtOAc. The organic layer was concentrated to dryness and combined with the precipitate. The material was purified on a silica gel cartridge using EtOAc:Hex as the eluent to afford a 19 white solid (324 mg, 18%). Mass Spec (lo-res): Calc'd for C8H8N4O3: 208.06; found: 209.10 (M+H). the resultant precipitate (1.2 g) was filtered off washed with water (2×40 mL) The aqueous layer was extracted into EtOAc The organic layer was concentrated to dryness The material was purified on a silica gel cartridge

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

Procedure: To a solution of 2-bromo-N-(prop-2-yn-1-yl)acetamide (0.7 g, 3.98 mmol) in DCM (10 mL) added N-methyl piperazine (0.66 mL, 5.96 mmol) drop wise. Reaction mixture stirred at rt for 16 h, diluted with DCM and washed with water and brine. The organic layer was dried over Na2SO4 and concentrated in vacuo. The crude residue was triturated with ether-pentane, affording the title compound (0.38 g, 49%); LCMS: m/z=196.15 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 8.06 (d, J=6.1 Hz, 1H), 3.86 (dd, J=5.9, 2.5 Hz, 2H), 3.07 (t, J=2.5 Hz, 1H), 2.91 (s, 2H), 2.47-2.25 (m, 8H), 2.15 (s, 3H). Reaction mixture washed with water and brine The organic layer was dried over Na2SO4 concentrated in vacuo The crude residue was triturated with ether-pentane

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

Procedure: To a solution of 2-bromo-N-(prop-2-yn-1-yl)acetamide (0.6 g, 3.4 mmol) in acetonitrile (5 mL) was added trimethylamine (30% in MeOH, 5 mL). The mixture was stirred at room temperature for 16 h and concentrated in vacuo. The resulting residue was triturated with ether, resulting in the title compound (780 mg, 97%); LCMS: m/z=155.1 (M+1); 1H NMR (300 MHz, DMSO-d6) δ 9.03 (t, J=5.3 Hz, 1H), 4.17 (s, 2H), 3.95 (dd, J=5.4, 2.6 Hz, 2H), 3.23 (s, 9H), 2.09 (s, 1H). concentrated in vacuo The resulting residue was triturated with ether