(CYCLOPROPYLMETHYL)HYDRAZINE DIHYDROCHLORIDE

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

Procedure: A mixture of Example 1B (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.7 g, 93 mmol) in ethanol (100 mL) was heated at reflux for 6 hours. The mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate (20 mL). The resulting white precipitate was filtered, washed with ether, and dried to yield 17.5 g (90%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4 H), 1.16-1.27 (m, 1 H), 1.28 (s, 9 H), 4.38 (d, J=7.12 Hz, 2 H), 4.80 (br, 2 H), 5.53 (s, 1 H), 15.5 (br, 1 H); MS (DCI) m/z 194 [M+H]+. at reflux for 6 hours concentrated under reduced pressure The residue was diluted with ethyl acetate (20 mL) The resulting white precipitate was filtered washed with ether dried

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

Procedure: A mixture of Example 1B (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.7 g, 93 mmol) in ethanol (100 mL) was heated at reflux for 6 hours. The mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate (20 mL). The resulting white precipitate was filtered, washed with ether, and dried to yield 17.5 g (90%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4 H), 1.16-1.27 (m, 1 H), 1.28 (s, 9 H), 4.38 (d, J=7.12 Hz, 2 H), 4.80 (br, 2 H), 5.53 (s, 1 H), 15.5 (br, 1 H); MS (DCI) m/z 194 [M+H]+. at reflux for 6 hours concentrated under reduced pressure The residue was diluted with ethyl acetate (20 mL) The resulting white precipitate was filtered washed with ether dried

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

Procedure: A mixture of Example 27B (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.69 g, 93 mmol) in ethanol (50 mL) was refluxed at 90° C. for 6 hours. The mixture was concentrated under reduced pressure and ethyl acetate (20 mL) added to the residue. The white solid precipitate was filtered, washed with ether and dried to yield 17.5 g (90%) of title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4H), 1.16-1.27 (m, 1H), 1.28 (s, 9H), 4.02 (d, J=7.12 Hz, 2H), 5.53 (s, 1H), 6.91 (s, 2H), 14.05 (s, 1H); MS (DCI) m/z 294 [M+H]+. The mixture was concentrated under reduced pressure and ethyl acetate (20 mL) added to the residue The white solid precipitate was filtered washed with ether dried

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

Procedure: A mixture of Example 9B (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.69 g, 93 mmol) in ethanol (100 mL) was heated at reflux (oil bath temperature of 90° C.) for 6 hours. The mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate (20 mL). The resulting white solid was collected by filtration (Et2O wash) and dried to provide 17.5 g (90%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4H), 1.16-1.27 (m, 1H), 1.28 (s, 9H), 4.02 (d, J=7.12 Hz, 2H), 5.53 (s, 1H), 6.91 (s, 2H), 14.05 (s, 1H); MS (DCI) m/z 294 [M+H]+. The mixture was cooled to room temperature concentrated under reduced pressure The residue was diluted with ethyl acetate (20 mL) The resulting white solid was collected by filtration (Et2O wash) dried

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

Procedure: A mixture of Example 3A (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.7 g, 93 mmol) in ethanol (100 mL) was heated at reflux for 6 hours. The mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate (20 mL). The resulting white precipitate was filtered, washed with ether, and dried to yield 17.5 g (90%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4H), 1.16-1.27 (m, 1H), 1.28 (s, 9H), 4.38 (d, J=7.12 Hz, 2H), 4.80 (br, 2H), 5.53 (s, 1H), 15.5 (br, 1H); MS (DCI) m/z 194 [M+H]+. at reflux for 6 hours concentrated under reduced pressure The residue was diluted with ethyl acetate (20 mL) The resulting white precipitate was filtered washed with ether dried

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

Procedure: A mixture of Example 27B (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.69 g, 93 mmol) in ethanol (50 mL) was refluxed at 90° C. for 6 hours. The mixture was concentrated under reduced pressure and ethyl acetate (20mL) added to the residue. The white solid precipitate was filtered, washed with ether and dried to yield 17.5 g (90%) of title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4H), 1.16-1.27 (m, 1H), 1.28 (s, 9H), 4.02 (d, J=7.12 Hz, 2H), 5.53 (s, 1H), 6.91 (s, 2H), 14.05 (s, 1H); H); MS (DCI) m/z 294 [M+H]+. The mixture was concentrated under reduced pressure and ethyl acetate (20mL) added to the residue The white solid precipitate was filtered washed with ether dried

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

Procedure: A mixture of Example 1B (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.7 g, 93 mmol) in ethanol (100 mL) was heated at reflux for 6 hours. The mixture was cooled to room temperature, and concentrated under reduced pressure. The residue was diluted with ethyl acetate (20 mL). The resulting white precipitate was filtered, washed with ether, and dried to yield 17.5 g (90%) of title compound. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4 H), 1.16-1.27 (m, 1 H), 1.28 (s, 9 H), 4.38 (d, J=7.12 Hz, 2 H), 4.80 (br, 2 H), 5.53 (s, 1 H), 15.5 (br, 1 H); MS (DCI) m/z 194 [M+H]+. at reflux for 6 hours concentrated under reduced pressure The residue was diluted with ethyl acetate (20 mL) The resulting white precipitate was filtered washed with ether dried

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

Procedure: A mixture of Example 27B (13.5 g, 85 mmol) and 4,4-dimethyl-3-oxopentanenitrile (11.69 g, 93 mmol) in ethanol (50 mL) was refluxed at 90° C. for 6 hours. The mixture was concentrated under reduced pressure and ethyl acetate (20 mL) added to the residue. The white solid precipitate was filtered, washed with ether and dried to yield 17.5 g (90%) of title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 0.42-0.54 (m, 4H), 1.16-1.27 (m, 1H), 1.28 (s, 9H), 4.02 (d, J=7.12 Hz, 2H), 5.53 (s, 1H), 6.91 (s, 2H), 14.05 (s, 1H); MS (DCI) m/z 294 [M+H]+. The mixture was concentrated under reduced pressure and ethyl acetate (20 mL) added to the residue The white solid precipitate was filtered washed with ether dried