Reaction SMILES: [NH2:1]C1C=CN=CC=1.C(N(CC)CC)C.Cl[C:16]([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])=[O:17]>C(Cl)Cl>[C:16](=[O:17])([O:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[NH2:1]
Reactant: CCCCCCCCCCCCOC(=O)Cl
Reactant: Nc1ccncc1
Solvent: ClCCl
Solvent: CCN(CC)CC
Product: CCCCCCCCCCCCOC(N)=O
Temperature: 25 °C
Yield: 120.3 %

Procedure:
To a solution of 4-aminopyridine (2.00 g, 21.2 mmol) in CH2Cl2 (50 mL) at 0° C. was added triethylamine (3.50 mL, 25.0 mmol) and isopropyl chloroformate (22.0 mL, 1.0 M in toluene). The ice bath was removed and the resulting mixture was allowed to warm to rt over 2 h. The reaction mixture was filtered through a plug of silica gel (EtOAc) then concentrated. The crude product was recrystallized from EtOAc to give 1.90 g (50% yield) of pure isopropyl carbamate. Synthesis of N-(4-Pyridyl) Dodecyl Carbamate (5). To a solution of 4-aminopyridine (3.00 g, 31.9 mmol) in CH2Cl2 (50 mL) at 0° C. was added triethylamine (5.60 mL, 40.0 mmol) and dodecyl chloroformate (8.70 g, 35.0 mmol). The ice bath was removed and the resulting mixture was allowed to warm to rt over 3 h before being poured into saturated aqueous NaHCO3. The product was extracted with CH2Cl2, washed with brine, dried (MgSO4) and concentrated. The crude product was recrystallized from EtOAc/hexanes to give 8.80 g (90% yield) of pure dodecyl carbamate. Synthesis of N-(4-Pyridyl) Benzyl Carbamate (6). To a solution of 4-aminopyridine (2.00 g, 21.2 mmol) in CH2Cl2 (30 mL) at 0° C. was added triethylamine (3.50 mL, 25.0 mmol) and benzyl chloroformate (3.10 mL, 22.0 mmol). The ice bath was removed and the resulting mixture was allowed to warm to rt overnight before being poured into saturated aqueous NaHCO3. The product was extracted with CH2Cl2, dried (Na2SO4) and concentrated. The crude product was recrystallized from EtOAc to give 2.90 g (60% yield) of pure benzyl carbamate. Synthesis of N-(4-Pyridyl) Benzamide (7). To a solution of 4-aminopyridine (3.00 g, 31.9 mmol) in CH2Cl2 (50 mL) at 0° C. was added triethylamine (6.70 mL, 47.9 mmol) and benzoyl chloride (3.70 mL, 31.9 mmol). The ice bath was removed and the resulting mixture was allowed to warm tort over 1.5 h. The reaction was quenched with saturated aqueous NaHCO3, extracted with CH2Cl2, washed with brine, dried (MgSO4) and concentrated. The crude product was recrystallized from EtOAc/hexanes to give 4.73 g (75% yield) of pure benzamide. Synthesis of N-(4-Pyridyl) Acetamide (8). To a solution of 4-aminopyridine (2.00 g, 21.2 mmol) in CH2Cl2 (30 mL) at 0° C. was added triethylamine (3.60 mL, 25.6 mmol) and acetic anhydride (2.20 mL, 23.2 mmol). The ice bath was removed and the resulting mixture was allowed to warm to rt overnight before being poured into saturated aqueous NaHCO3. The mixture was stirred for 15 min then the layers were separated. The aqueous layer was extracted with CH2Cl2 twice more in the same fashion. The combined organic layers were dried (Na2SO4) and concentrated. The crude product was recrystallized from EtOAc to give 1.60 g (56% yield) of pure acetamide. Synthesis of N-(4-Pyridyl) Propionamide (9). To a solution of 4-aminopyridine (3.00 g, 31.9 mmol) in CH2Cl2 (30 mL) at 0° C. was added triethylamine (6.70 mL, 47.8 mmol) and propionyl chloride (3.30 mL, 38.2 mmol). The ice bath was removed and the resulting mixture was allowed to warm to rt over 4 h before being poured into saturated aqueous NaHCO3. The mixture was stirred for 45 min and was filtered. The filter cake was recrystallized from EtOAc to give 1.65 g (50% yield) of pure propionamide. Synthesis of N-(4-Pyridyl) Trimethylacetamide (10). To a solution of 4-aminopyridine (2.00 g, 21.2 mmol) in CH2Cl2 (30 mL) at 0° C. was added triethylamine (3.50 mL, 25.0 mmol) and pivaloyl chloride (2.70 mL, 23.2 mmol). The ice bath was removed and the resulting mixture was allowed to warm to rt overnight before being poured into saturated aqueous NaHCO3. The mixture was stirred for 5 min then the layers were separated. The aqueous layer was extracted with CH2Cl2 twice more in the same fashion. The combined organic layers were dried (Na2SO4) and concentrated. The crude product was recrystallized from EtOAc to give 1.40 g (37% yield) of pure trimethylacetamide. Synthesis of N-(4-Pyridyl) Ethyl Succinamate (11). To a solution of 4-aminopyridine (1.50 g, 16.0 mmol) in CH2Cl2 (50 mL) was added triethylamine (3.50 mL, 25.0 mmol) and ethyl-4-oxo-4-chlorobutyrate (2.25 mL, 16.0 mmol). The resulting mixture was allowed to stir for 1.5 h before being poured into saturated aqueous NaHCO3. The mixture was stirred for 5 min then the layers were separated. The aqueous layer was extracted twice more with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated. The crude product was recrystallized from EtOAc/hexanes to give 590 mg (17% yield) of pure succinamate. Synthesis of N,N′-(4-Pyridyl) Urea (12). A mixture of 4-aminopyridine (3.00 g, 31.9 mmol) and carbonyldiimidazole (5.17 g, 32.0 mmol) in benzene (50 mL) was refluxed for 5 h. The reaction mixture was concentrated and the crude product was recrystallized from H2O to give 1.60 g(47% yield) of pure urea. Synthesis of N,N′-(3,4-Pyridyl) Urea (13). A mixture of 3,4-diaminopyridine (2.50 g, 23.0 mmol) and carbonyldiimidazole (7.50 g, 46.0 mmol) in benzene (50 mL) was refluxed for 4 h before being poured into H2O. The resulting mixture was acidified with 1.0 M HCl and the layers were separated. The pH of the aqueous layer was adjusted to ˜40 wit saturated aqueous NaHCO3 then the solution was concentrated. The solid products were dried under high vacuum for 16 h then were slurried with hot MeOH. The slurried mixture was filtered and the filtrated was concentrated. The crude product was recrystallized from H2O to give 2.63 g (85% yield) of pure urea. Synthesis of P,P-Diphenyl N-(4-Pyridyl) Phosphinamide (14). To a solution of 4-aminopyridine (1.00 g, 10.6 mmol) in CH2Cl2 (30 mL) was added triethylamine (1.70 mL, 12.0 mmol) and diphenylphosphinic chloride (2.00 mL, 10.6 mmol). The reaction mixture was allowed to stir for 6 h before being poured into saturated aqueous NaHCO3. The resulting mixture was stirred for 15 min then the layers were separated. The aqueous layer was extracted twice more with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated. The crude product was recrystallized from MeOH/H2O to give 2.69 g (86% yield) of pure phosphinamide. Synthesis of 4-Pyridinyl Phosphoramidic acid, Diphenyl Ester (15). To a solution of 4-aminopyridine (1.00 g, 10.6 mmol) in CH2Cl2 (30 mL) was added triethylamine (2.20 mL, 16.0 mmol) and diphenylchlorophosphate (2.30 mL, 11.0 mmol). The reaction mixture was allowed to stir for 3 h before being poured into saturated aqueous NaHCO3. The resulting mixture was stirred for 15 min then the layers were separated. The aqueous layer was extracted twice more with CH2Cl2. The combined organic layers were dried (Na2SO4) and concentrated. The crude product was recrystallized from MeOH/H2O to give 1.36 g (39% yield) of pure phosphoramidic acid diester.