9H-fluoren-9-ylmethyl N-(sulfanylidenemethylidene)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:

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:

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

Procedure: 6.67 g (31.7 mmol) of ethyl 2-aminomethyl-6-methoxyisonicotinate (20d) were dissolved in 175 ml of toluene and treated at RT with 8.93 g (281.3 mmol) of fluoren-9-ylmethyloxycarbonyl isothiocyanate. After 15 minutes, the resulting precipitate was filtered off and dried at 50° C., 4.6 g of the title compound being isolated. The filtrate was concentrated, and the residue was taken up in DCM and washed three times with water. The organic phase was dried with MgSO4 and concentrated. The crude product thus obtained was chromatographed on silica gel (heptane/ethyl acetate 90:10→75:25), it being possible to isolate a further 8.1 g of the title compound. the resulting precipitate was filtered off dried at 50° C.

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

Procedure: 6.67 g (31.7 mmol) of ethyl 2-aminomethyl-6-methoxyisonicotinate (20d) were dissolved in 175 ml of toluene and treated at RT with 8.93 g (281.3 mmol) of fluoren-9-ylmethyloxycarbonyl isothiocyanate. After 15 minutes, the resulting precipitate was filtered off and dried at 50° C., 4.6 g of the title compound being isolated. The filtrate was concentrated, and the residue was taken up in DCM and washed three times with water. The organic phase was dried with MgSO4 and concentrated. The crude product thus obtained was chromatographed on silica gel (heptane/ethyl acetate 90:10→75:25), it being possible to isolate a further 8.1 g of the title compound. the resulting precipitate was filtered off dried at 50° C.

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

Procedure: 500 mg (2.39 mmol) of 6-aminomethyl-4-ethoxy-N-methylnicotinamide (Example 12f) were dissolved in 25 ml of dioxane and treated at RT with 672.4 mg (2.39 mmol) of fluoren-9-ylmethyloxycarbonyl isothiocyanate. After one hour, the mixture was freed from the solvent and the residue was taken up in DCM. It was washed three times with aqueous LiCl solution and once with water. After drying with MgSO4, the mixture was concentrated and the crude product (875 mg) thus obtained was reacted further without further purification. It was washed three times with aqueous LiCl solution After drying with MgSO4 the mixture was concentrated

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

Procedure: 500 mg (2.39 mmol) of 6-aminomethyl-4-ethoxy-N-methylnicotinamide (Example 12f) were dissolved in 25 ml of dioxane and treated at RT with 672.4 mg (2.39 mmol) of fluoren-9-ylmethyloxycarbonyl isothiocyanate. After one hour, the mixture was freed from the solvent and the residue was taken up in DCM. It was washed three times with aqueous LiCl solution and once with water. After drying with MgSO4, the mixture was concentrated and the crude product (875 mg) thus obtained was reacted further without further purification. It was washed three times with aqueous LiCl solution After drying with MgSO4 the mixture was concentrated