2-methylpropane-1,3-diamine

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ 0.89 (d, 3H, CH3), 1.22 [s, 6H, C(CH3)2], 1.51 (m, 1H, CH3CH), 2.25 (d, 2H, CH2NH2), 2.65 (m, 2H, NHCH2), 5.31 (s, 2H, imi-CH2), 7.03 & 7.21 (2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ 0.89 (d, 3H, CH3), 1.22 [s, 6H, C(CH3)2], 1.51 (m, 1H, CH3CH), 2.25 (d, 2H, CH2NH2), 2.65 (m, 2H, NHCH2), 5.31 (s, 2H, imi-CH2), 7.03 & 7.21 (2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ 0.89 (d, 3H, CH3), 1.22 [s, 6H, C(CH3)2], 1.51 (m, 1H, CH3CH), 2.25 (d, 2H, CH2NH2), 2.65 (m, 2H, NHCH2), 5.31 (s, 2H, imi-CH2), 7.03 & 7.21 (2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ 0.89 (d, 3H, CH3), 1.22 [s, 6H, C(CH3)2], 1.51 (m, 1H, CH3CH), 2.25 (d, 2H, CH2NH2), 2.65 (m, 2H, NHCH2), 5.31 (s, 2H, imi-CH2), 7.03 & 7.21 (2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ 0.89 (d, 3H, CH3), 1.22 [s, 6H, C(CH3)2], 1.51 (m, 1H, CH3CH), 2.25 (d, 2H, CH2NH2), 2.65 (m, 2H, NHCH2), 5.31 (s, 2H, imi-CH2), 7.03 & 7.21 (2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ0.89(d, 3H, CH3), 1.22[s, 6H, C(CH3)2], 1.51(m, 1H, CH3CH), 2.25(d, 2H, CH2NH2), 2.65(m, 2H, NHCH2), 5.31(s, 2H, imi-CH2), 7.03 & 7.21(2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ0.89(d, 3H, CH3), 1.22[s, 6H, C(CH3)2], 1.51(m, 1H, CH3CH), 2.25(d, 2H, CH2NH2), 2.65(m, 2H, NHCH2), 5.31(s, 2H, imi-CH2), 7.03 & 7.21(2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102°-104° C. (decomp); 1H NMR (CDCl3) δ 0.89 (d, 3H, CH3), 1.22[s, 6H, C(CH3)2 ], 1.51 (m, 1H, CH3CH), 2.25 (d, 2H, CH2NH2), 2.65 (m, 2H, NHCH2), 5.31 (s, 2H, imi-CH2), 7.03 & 7.21 (2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102°-104° C. (decomp); 1H NMR (CDCl3) δ 0.89 (d, 3H, CH3), 1.22[s, 6H, C(CH3)2 ], 1.51 (m, 1H, CH3CH), 2.25 (d, 2H, CH2NH2), 2.65 (m, 2H, NHCH2), 5.31 (s, 2H, imi-CH2), 7.03 & 7.21 (2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: Anhydrous ethanol (460 mL) and sodium (0.57 g, 25 mmol, 0.1 eq) were added to a round bottom flask and stirred under argon until all of the sodium disappeared. 4-nitrobenzonitrile (38.0 g, 257 mmol, 1.0 eq) was then added. The suspension was stirred for 15 h at room temperature under argon. 1,3-diamino-2-methylpropane (22.0 g, 249 mmol, 0.97 eq) was added. The mixture was heated to reflux for 4 days. After removal of the solvent under reduced pressure, the resulting red residue was mixed with ethyl acetate (800 mL) and extracted with 2N HCl (3×200 mL). The combined aqueous mixture was washed with ethyl acetate (250 mL) and the organic layer was removed. The acidic aqueous mixture was basified with solid Na2CO3 and then 5N NaOH until pH was 13. The emulsion was extracted with ethyl acetate (1×400 mL, 2×250 mL). The combined organic layers were washed with brine (400 mL) and then dried over Na2SO4. Upon concentrating, compound 3 was obtained as a yellow solid (12.8 g, 23% yield). The mixture was heated to reflux for 4 days After removal of the solvent under reduced pressure the resulting red residue was mixed with ethyl acetate (800 mL) extracted with 2N HCl (3×200 mL) The combined aqueous mixture was washed with ethyl acetate (250 mL) the organic layer was removed The emulsion was extracted with ethyl acetate (1×400 mL, 2×250 mL) The combined organic layers were washed with brine (400 mL) dried over Na2SO4 Upon concentrating

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ 0.89 (d, 3H, CH3), 1.22 [s, 6H, C(CH3)2], 1.51 (m, 1H, CH3CH), 2.25 (d, 2H, CH2NH2), 2.65 (m, 2H, NHCH2), 5.31 (s, 2H, imi-CH2), 7.03 & 7.21 (2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether

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

Procedure: 3-Chloro-3-methyl-1-(2-nitroimidazolyl)-2-nitrosobutane (1.5 g, 6.09 mmol, Example 1) was added portionwise over a period of 30 minutes to a stirred solution of 1,3-diamino-2-methylpropane (3.0 g, 34.10 mmol) in dry acetonitrile (30 mL) at 50° C. After the addition the reaction mixture was allowed to remain at 50° C. for an additional 30 minutes. The reaction mixture was then cooled and solvent was removed on a rotary evaporator to a give a paste. This was crystallized from dichloromethane-ether to afford the title product as a light yellow solid; yield: 1.36 g (75%); mp. 102-104° C. (decomp); 1H NMR (CDCl3) δ 0.89 (d, 3H, CH3), 1.22 [s, 6H, C(CH3)2], 1.51 (m, 1H, CH3CH), 2.25 (d, 2H, CH2NH2), 2.65 (m, 2H, NHCH2), 5.31 (s, 2H, imi-CH2), 7.03 & 7.21 (2s, 2H, imi-H). MS m/e 299 (M+H)+. After the addition the reaction mixture The reaction mixture was then cooled solvent was removed on a rotary evaporator to a give a paste This was crystallized from dichloromethane-ether