isocyanatomethylcyclohexane

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

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

Procedure: (Z)-1-(2-Amino-1,2-dicyanovinyl)-3-(cyclohexylmethyl)urea. 2,3-Diaminomaleonitrile (0.119 g, 1.10 mmol) and (isocyanatomethyl)cyclohexane (0.140 g, 1.00 mmol) in tetrahydrofuran (2 mL) were reacted according to General Procedure A. Dichloromethane and hexanes were added to the solution and the resultant precipitate was filtered and dried to afford the title compound (0.200 g, 47%). MS (ESI) m/z 248.2 [M+1]+. the resultant precipitate was filtered dried

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

Procedure: 1-Benzylimidazolidine-2,4-dione (100 mg, 0.526 mmol) and isocyanatomethylcyclohexane (87.8 mg, 0.63 mmol) were reacted in analogy to example 1. Yield: 36.8 mg (21%), M+H+: 330.18.

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

Procedure: Prepared by way of method III using 18-hydroxy-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo[14.3.0.04,6]-nonadec-7-ene (100 mg, 0.175 mmol) and cyclohexylmethyl isocyanate (53 μL, 0.35 mmol). The final trituration (diethyl ether/hexane) and filtration gave 36 mg (29%) of 18-cyclohexylmethylaminocarbonyloxyl-14-tert-butoxycarbonylamino-4-cyclopropylsulfonylaminocarbonyl-2,15-dioxo-3,16-diaza-10-oxatricyclo-[14.3.0.04,6]-nonadec-7-ene as a white powder: 99.0% pure (HPLC), MS m/z 708 (M−H)−, HRMS calcd. 708.3278 and found 708.3269, mp 142-144° C. Prepared by way of method III The final trituration (diethyl ether/hexane) and filtration

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

Procedure: (Z)-1-(2-Amino-1,2-dicyanovinyl)-3-(cyclohexylmethyl)urea. 2,3-Diaminomaleonitrile (0.119 g, 1.10 mmol) and (isocyanatomethyl)cyclohexane (0.140 g, 1.00 mmol) in tetrahydrofuran (2 mL) were reacted according to General Procedure A. Dichloromethane and hexanes were added to the solution and the resultant precipitate was filtered and dried to afford the title compound (0.200 g, 47%). MS (ESI) m/z 248.2 [M+1]+. the resultant precipitate was filtered dried

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

Procedure: (Z)-1-(2-Amino-1,2-dicyanovinyl)-3-(cyclohexylmethyl)urea. 2,3-Diaminomaleonitrile (0.119 g, 1.10 mmol) and (isocyanatomethyl)cyclohexane (0.140 g, 1.00 mmol) in tetrahydrofuran (2 mL) were reacted according to General Procedure A. Dichloromethane and hexanes were added to the solution and the resultant precipitate was filtered and dried to afford the title compound (0.200 g, 47%). MS (ESI) m/z 248.2 [M+1]+. the resultant precipitate was filtered dried

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

Procedure: (Z)-1-(2-Amino-1,2-dicyanovinyl)-3-(cyclohexylmethyl)urea. 2,3-Diaminomaleonitrile (0.119 g, 1.10 mmol) and (isocyanatomethyl)cyclohexane (0.140 g, 1.00 mmol) in tetrahydrofuran (2 mL) were reacted according to General Procedure A. Dichloromethane and hexanes were added to the solution and the resultant precipitate was filtered and dried to afford the title compound (0.200 g, 47%). MS (ESI) m/z 248.2 [M+1]+. the resultant precipitate was filtered dried

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

Procedure: The title compound was synthesized from 1-benzyl-3,3-dimethylindolin-5-ol (20.0 mg, 0.09 mmol) using the same procedure employed for Example 2 (2), but with cyclohexylmethylisocyanate instead of 4-isopropylphenylisocyanate. The product was obtained as a white solid (10.5 mg, 34%) having the following characteristics.

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

Procedure: The title compound was synthesized from 1-benzyl-3,3-dimethylindolin-5-ol (20.0 mg, 0.09 mmol) using the same procedure employed for Example 2 (2), but with cyclohexylmethylisocyanate instead of 4-isopropylphenylisocyanate. The product was obtained as a white solid (10.5 mg, 34%) having the following characteristics.

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

Procedure: The title compound was synthesized from 1-(4-pyridylmethyl)-3,3-dimethylindolin-5-ol (20.0 mg, 0.09 mmol) using the same procedure employed for Example 2 (2), but with cyclohexylmethylisocyanate instead of 4-isopropylphenylisocyanate. The product was obtained as a white solid (5.8 mg, 19%) having the following characteristics.

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

Procedure: The title compound was synthesized from 1-(4-pyridylmethyl)-3,3-dimethylindolin-5-ol (20.0 mg, 0.09 mmol) using the same procedure employed for Example 2 (2), but with cyclohexylmethylisocyanate instead of 4-isopropylphenylisocyanate. The product was obtained as a white solid (5.8 mg, 19%) having the following characteristics.

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

Procedure: The title compound was synthesized from 1-(3-pyridylmethyl)-3,3-dimethylindolin-5-ol (20.0 mg, 0.09 mmol) using the same procedure employed for Example 2 (2), but with cyclohexylmethylisocyanate instead of 4-isopropylphenylisocyanate. The product was obtained as a white solid (11.6 mg, 38%) having the following characteristics.