tert-butyl N-(3-cyanopropyl)carbamate

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: This compound was synthesized in an analogous manner to Example 32 but using tert-butyl 3-cyanopropylcarbamate instead of acetonitrile in the preparation of 2-propen-1-yl (4-(2-((tert-butoxycarbonyl)amino)ethyl)-3-(6-isoquinolinyl)-5-isoxazolyl)carbamate according to Scheme 6 instead of allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate. MS m/z: 527 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.75 (s, 1H), 8.63 (d, J=6.26 Hz, 1H), 8.51-8.57 (m, 3H), 8.20 (d, J=8.61 Hz, 1H), 7.61 (d, J=8.02 Hz, 1H), 7.40 (d, J=8.22 Hz, 1H), 7.26-7.29 (m, 1H), 7.15 (t, J=7.53 Hz, 1H), 7.08 (t, J=7.43 Hz, 1H), 3.73-3.86 (m, 3H), 3.13-3.24 (m, 4H), 2.62 (t, J=6.94 Hz, 2H), 1.33 (s, 9H). This compound was synthesized in an analogous manner to Example 32

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

Procedure: This compound was synthesized in an analogous manner to Example 32 but using tert-butyl 3-cyanopropylcarbamate instead of acetonitrile in the preparation of 2-propen-1-yl (4-(2-((tert-butoxycarbonyl)amino)ethyl)-3-(6-isoquinolinyl)-5-isoxazolyl)carbamate according to Scheme 6 instead of allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate. MS m/z: 527 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.75 (s, 1H), 8.63 (d, J=6.26 Hz, 1H), 8.51-8.57 (m, 3H), 8.20 (d, J=8.61 Hz, 1H), 7.61 (d, J=8.02 Hz, 1H), 7.40 (d, J=8.22 Hz, 1H), 7.26-7.29 (m, 1H), 7.15 (t, J=7.53 Hz, 1H), 7.08 (t, J=7.43 Hz, 1H), 3.73-3.86 (m, 3H), 3.13-3.24 (m, 4H), 2.62 (t, J=6.94 Hz, 2H), 1.33 (s, 9H). This compound was synthesized in an analogous manner to Example 32

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL of round-bottom flask was added tert-butyl 3-bromopropylcarbamate (4.0 g, 17 mmol) (commercially available from 3B Scientific Corporation Product List Order Number 3B3-073730), potassium cyanide (1.5 mL, 20 mmol) and 100 mL of DMSO. The reaction mixture was heated at 90° C. for 16 hours. The mixture was then diluted with 100 mL of water, and extracted with 100 mL of EtOAc twice. The extracts were combined, concentrated, and purified by flash chromatography on silica gel (40% EtOAc/hexane) to give tert-butyl 3-cyanopropylcarbamate (1.7 g, 55% yield). MS m/z: 185 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 4.70 (br s, 1H), 3.25 (q, J=6.65 Hz, 2H), 2.40 (t, J=7.24 Hz, 2H), 1.84-1.91 (m, 2H), 1.45 (s, 9H). extracted with 100 mL of EtOAc twice concentrated purified by flash chromatography on silica gel (40% EtOAc/hexane)

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

Procedure: This compound was synthesized in an analogous manner to Example 32 but using tert-butyl 3-cyanopropylcarbamate instead of acetonitrile in the preparation of 2-propen-1-yl (4-(2-((tert-butoxycarbonyl)amino)ethyl)-3-(6-isoquinolinyl)-5-isoxazolyl)carbamate according to Scheme 6 instead of allyl 3-(isoquinolin-6-yl)isoxazol-5-ylcarbamate. MS m/z: 527 (M+1); 1H NMR (400 MHz, CD3OD) δ ppm 9.75 (s, 1H), 8.63 (d, J=6.26 Hz, 1H), 8.51-8.57 (m, 3H), 8.20 (d, J=8.61 Hz, 1H), 7.61 (d, J=8.02 Hz, 1H), 7.40 (d, J=8.22 Hz, 1H), 7.26-7.29 (m, 1H), 7.15 (t, J=7.53 Hz, 1H), 7.08 (t, J=7.43 Hz, 1H), 3.73-3.86 (m, 3H), 3.13-3.24 (m, 4H), 2.62 (t, J=6.94 Hz, 2H), 1.33 (s, 9H). This compound was synthesized in an analogous manner to Example 32

Conditions: temp:90.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a 250 mL of round-bottom flask was added tert-butyl 3-bromopropylcarbamate (4.0 g, 17 mmol) (commercially available from 3B Scientific Corporation Product List Order Number 3B3-073730), potassium cyanide (1.5 mL, 20 mmol) and 100 mL of DMSO. The reaction mixture was heated at 90° C. for 16 hours. The mixture was then diluted with 100 mL of water, and extracted with 100 mL of EtOAc twice. The extracts were combined, concentrated, and purified by flash chromatography on silica gel (40% EtOAc/hexane) to give tert-butyl 3-cyanopropylcarbamate (1.7 g, 55% yield). MS m/z: 185 (M+1); 1H NMR (400 MHz, CDCl3) δ ppm 4.70 (br s, 1H), 3.25 (q, J=6.65 Hz, 2H), 2.40 (t, J=7.24 Hz, 2H), 1.84-1.91 (m, 2H), 1.45 (s, 9H). extracted with 100 mL of EtOAc twice concentrated purified by flash chromatography on silica gel (40% EtOAc/hexane)