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Product Details of [ 58483-97-9 ]

CAS No. :58483-97-9 MDL No. :MFCD18260978
Formula : C6H6ClN3O Boiling Point : -
Linear Structure Formula :- InChI Key :JFNZMPQWXSLMHC-UHFFFAOYSA-N
M.W : 171.58 Pubchem ID :66876883
Synonyms :

Safety of [ 58483-97-9 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P264-P280-P302+P352-P305+P351+P338-P332+P313-P337+P313-P362 UN#:N/A
Hazard Statements:H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 58483-97-9 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 58483-97-9 ]

[ 58483-97-9 ] Synthesis Path-Downstream   1~50

  • 1
  • [ 99613-64-6 ]
  • [ 58483-97-9 ]
  • [ 1021873-82-4 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 100.0℃; for 14.0h; Example 185 5-chloro-1-(4-chloro-3-cyanobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added <strong>[99613-64-6]5-(bromomethyl)-2-chlorobenzonitrile</strong> (0.31 g), and the mixture was stirred at 100C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (93 mg). 1H-NMR (DMSO-d6) d ppm 5.57 (2H, s), 7.69 (1H, dd, J=8.5, 2.3 Hz), 7.78-7.86 (1H, m), 7.97 (1H, d, J=2.3 Hz), 8.21 (1H, s), 8.55-8.67 (2H, m), 8.77 (1H, d, J=2.3 Hz), 9.44 (2H, br-s).
  • 2
  • [ 58483-97-9 ]
  • [ 53606-06-7 ]
  • [ 1021873-44-8 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 8h; 150 Example 150 5-chloro-2-imino-1-[4-(methylsulfonyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 1-(bromomethyl)-4-(methylsulfonyl)benzene (0.33 g), and the mixture was stirred at 100°C for 8 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (126 mg). 1H-NMR (DMSO-d6) d ppm 3.23 (3 H, s) 5.66 (2 H, s) 7.52 (2 H, d, J=8.33 Hz) 7.96 (2 H, d, J=8.33 Hz) 8.21 (1 H, s) 8.59 (1 H, s) 8.64 (1 H, d, J=1.89 Hz) 8.82 (1 H, d, J=2.27 Hz) 9.42 (2 H, s).
  • 3
  • [ 294860-49-4 ]
  • [ 58483-97-9 ]
  • [ 1021873-54-0 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 4h; 152 Example 152 5-chloro-2-imino-1-[2-methoxy-5-(methylsulfonyl)benzyl]-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 2-(bromomethyl)-1-methoxy-4-(methylsulfonyl)benzene (0.29 g), and the mixture was stirred at 100°C for 4 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (110 mg). 1H-NMR (DMSO-d6) d ppm 3.17 (3 H, s) 3.92 (3 H, s) 5.47 (2 H, s) 7.74 (1 H, s) 7.98 (1 H, dd, J=8.67, 2.26 Hz) 8.21 (1 H, s) 8.59-8.66 (3 H, m) 9.40 (2 H, s).
  • 4
  • [ 58483-97-9 ]
  • [ 212268-39-8 ]
  • [ 1021873-66-4 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 24h; 172 Example 172 5-chloro-1-(3-fluoro-5-methylbenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide A solution of 2-amino-5-chloronicotinamide (150 mg) and 1-(bromomethyl)-3-fluoro-5-methylbenzene (270 mg) in DMF (3 ml) was stirred at 100°C for 24 hr. After cooling to room temperature, ethyl acetate was added, and the precipitated crystals were filtered and recrystallized to give the title compound (139 mg). 1H-NMR (DMSO-d6) d ppm 2.32 (3H, s), 5.49 (2H, s), 6.90-7.12 (3H, m), 8.20 (1H, s), 8.57 (1H, s), 8.62 (1H, d, J= 2.3 Hz), 8.75 (1H, d, J= 2.3 Hz), 9.19-9.61 (2H, m).
  • 5
  • [ 58483-97-9 ]
  • [ 180302-35-6 ]
  • [ 1021873-75-5 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 14h; 183 Example 183 5-chloro-1-(3-cyano-4-fluorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 5-(bromomethyl)-2-fluorobenzonitrile (0.29 g), and the mixture was stirred at 100°C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (71 mg). 1H-NMR (DMSO-d6) d ppm 5.56 (2H, s), 7.61 (1H, t, J=9.0 Hz), 7.74-7.84 (1H, m), 7.94 (1H, dd, J=2.3, 6.0 Hz), 8.21 (1H, s), 8.56-8.67 (2H, m), 8.78 (1H, d, J=2.3 Hz), 9.44 (2H, br-s).
  • 6
  • [ 58483-97-9 ]
  • [ 83311-25-5 ]
  • [ 1021873-79-9 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 100.0℃; for 14.0h; Example 184 5-chloro-1-(3-chloro-4-cyanobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-amino-5-chloronicotinamide (0.14 g) in N,N-dimethylformamide (3 ml) was added <strong>[83311-25-5]4-(bromomethyl)-2-chlorobenzonitrile</strong> (0.28 g), and the mixture was stirred at 100C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (85 mg). 1H-NMR (DMSO-d6) d ppm 5.60 (2H, s), 7.39 (1H, dd, J=8.0, 1.6 Hz), 7.75 (1H, d, J=1.6 Hz), 8.03 (1H, d, J=8.0 Hz), 8.20 (1H, s), 8.52-8.67 (2H, m), 8.74 (1H, s), 9.24-9.64 (2H, m).
  • 7
  • [ 180200-86-6 ]
  • [ 58483-97-9 ]
  • [ 1021873-50-6 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 4h; 154 Example 154 5-chloro-1-[2-chloro-4-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 1-(bromomethyl)-2-chloro-4-(methylsulfonyl)benzene (0.37 g), and the mixture was stirred at 100°C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (90 mg). 1H-NMR (DMSO-d6) d ppm 3.31 (3 H, s) 5.61 (2 H, s) 7.04 - 7.21 (1 H, m) 7.73 - 7.89 (1 H, m) 8.10 - 8.18 (1 H, m) 8.20 - 8.30 (1 H, m) 8.59 - 8.65 (1 H, m) 8.66 - 8.74 (2 H, m) 9.59 (2 H, s).
  • 8
  • [ 856935-35-8 ]
  • [ 58483-97-9 ]
  • [ 1021873-46-0 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 14h; 156 Example 156 5-chloro-1-(5-cyano-2-fluorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 3-(bromomethyl)-4-fluorobenzonitrile (0.29 g), and the mixture was stirred at 100°C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (60 mg). 1H-NMR (DMSO-d6) d ppm 5.59 (2H, s), 7.59 (1H, dd, J= 10.2, 8.7 Hz), 7.71 (1H, dd, J= 7.2, 1.9 Hz), 7.94-8.06 (1H, m), 8.23 (1H, s), 8.61 (1H, s), 8.64-8.70 (2H, m), 9.29-9.77 (2H, m).
  • 9
  • [ 849035-64-9 ]
  • [ 58483-97-9 ]
  • [ 1021873-43-7 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 14h; 149 Example 149 5-chloro-1-[4-chloro-2-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrobromide To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 1-(bromomethyl)-4-chloro-2-(methylsulfonyl)benzene (0.37 g), and the mixture was stirred at 100°C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (50 mg). 1H-NMR (DMSO-d6) d ppm 3.46 (3 H, s) 5.82 (2 H, s) 7.04 (1 H, d, J=8.33 Hz) 7.76 (1 H, dd, J=8.33, 2.27 Hz) 8.08 (1 H, d, J=2.27 Hz) 8.24 (1 H, s) 8.63 (1 H, s) 8.67 (2 H, d, J=4.16 Hz) 9.58 (2 H, s).
  • 10
  • [ 58483-97-9 ]
  • [ 1021871-31-7 ]
  • [ 1021873-51-7 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 12h; 157.3 (Step 3) To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 3-(bromomethyl)-5-chloro-N-methylbenzamide (0.28 g), and the mixture was stirred at 100°C for 12 hr. The reaction mixture was diluted with ethyl acetate. The solvent was removed, and the obtained precipitate was dissolved in methanol and crystallized from ethyl acetate. The obtained crystals were recrystallized from methanol-ethyl acetate to give the title compound (0.11 g). 1H-NMR (DMSO-d6) d ppm 2.77 (3 H, d, J=4.52 Hz) 5.57 (2 H, s) 7.60 (1 H, s) 7.66 (1 H, s) 7.89 (1 H, s) 8.21 (1 H, s) 8.52 - 8.69 (3 H, m) 8.81 (1 H, d, J=1.70 Hz) 9.41 (2 H, s).
  • 11
  • 2-(bromomethyl)-1-chloro-4-(methylsulfonyl)benzene [ No CAS ]
  • [ 58483-97-9 ]
  • [ 1021896-56-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-(bromomethyl)-1-chloro-4-(methylsulfonyl)benzene; 2-amino-5-chloropyridine-3-carboxamide In N,N-dimethyl-formamide at 100℃; for 4h; Stage #2: With water; sodium hydrogencarbonate 158 Example 158 5-chloro-1-[2-chloro-5-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 2-(bromomethyl)-1-chloro-4-(methylsulfonyl)benzene (0.30 g), and the mixture was stirred at 100°C for 4 hr. The reaction mixture was quenched with aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was treated by silica gel chromatography (ethyl acetate100%→ethyl acetate:methanol=4:1) to give a yellow solid.
  • 12
  • [ 58483-97-9 ]
  • [ 105942-09-4 ]
  • [ 1021873-61-9 ]
YieldReaction ConditionsOperation in experiment
Example 171 5-chloro-1-(4-cyano-2-fluorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride A solution of 2-amino-5-chloronicotinamide (150 mg) and <strong>[105942-09-4]4-(bromomethyl)-3-fluorobenzonitrile</strong> (282 mg) in DMF (3 ml) was stirred at 100C for 24 hr. After cooling to room temperature, ethyl acetate was added, and the precipitated crystals were filtered. The obtained crystals were dissolved in methanol (3 ml) and partitioned between ethyl acetate and aqueous sodium hydrogen carbonate solution. The organic layer was dried over magnesium sulfate and filtered. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/methanol=1/0 - 9/1). 4N Hydrochloric acid-ethyl acetate solution was added to the obtained yellow oil, and the precipitated crystals were filtered and recrystallized to give the title compound (47 mg). 1H-NMR (DMSO-d6) d ppm 5.70 (2H, s), 7.27 (1H, t, J= 7.9 Hz), 7.72 (1H, dd, J= 7.9, 1.2 Hz), 8.00 (1H, dd, J= 10.4, 1.2 Hz), 8.23 (1H, s), 8.67-8.77 (3H, m), 9.62 (2H, br-s).
  • 13
  • [ 58483-97-9 ]
  • [ 28188-41-2 ]
  • [ 1021873-34-6 ]
YieldReaction ConditionsOperation in experiment
28% In N,N-dimethyl-formamide at 100℃; for 3h;
In N,N-dimethyl-formamide at 105℃; for 5h; 136.2 (Step 2) To a solution of 2-amino-5-chloronicotinamide (0.14 g) obtained in Step 1 in N,N-dimethylformamide (3 ml) was added 3-cyanobenzylbromide (0.19 g), and the mixture was stirred at 105°C for 5 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (85 mg). 1H-NMR (DMSO-d6) d ppm 5.60 (2 H, s) 7.64 (2 H, d, J=4.92 Hz) 7.79 - 7.90 (2 H, m) 8.21 (1 H, s) 8.60 (1 H, s) 8.65 (1 H, d, J=2.27 Hz) 8.80 (1 H, d, J=2.27 Hz) 9.44 (2 H, s).
  • 14
  • [ 58483-97-9 ]
  • [ 50712-69-1 ]
  • [ 1021873-80-2 ]
YieldReaction ConditionsOperation in experiment
Example 187 5-chloro-1-(4-chloro-2-cyanobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride To a solution of 2-amino-5-chloronicotinamide (0.16 g) in N,N-dimethylformamide (3 ml) was added <strong>[50712-69-1]2-(bromomethyl)-5-chlorobenzonitrile</strong> (0.32 g), and the mixture was stirred at 100C for 14 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=3:2 - 4:1). 2N Hydrochloric acid-methanol solution (1 ml) was added to the obtained yellow oil at room temperature, and the obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (3 mg). 1H-NMR (DMSO-d6) d ppm 5.75 (2H, s), 7.24 (1H, d, J=2.0 Hz), 7.68 (1H, dd, J=8.3, 2.0 Hz), 8.05 (1H, d, J=8.3 Hz), 8.23 (1H, s), 8.60-8.78 (3H, m), 9.38-9.81 (2H, m).
  • 15
  • [ 58483-97-9 ]
  • [ 50712-67-9 ]
  • [ 1021873-76-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-5-chloropyridine-3-carboxamide; 2-(bromomethyl)-4-chlorobenzonitrile In N,N-dimethyl-formamide at 100℃; for 14h; Stage #2: With water; sodium hydrogencarbonate at 20℃; Stage #3: With hydrogenchloride In methanol 186 Example 186 5-chloro-1-(5-chloro-2-cyanobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 2-(bromomethyl)-4-chlorobenzonitrile (0.31 g), and the mixture was stirred at 100°C for 14 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=3:2 - 4:1). 2N Hydrochloric acid-methanol solution (1 ml) was added to the obtained yellow oil at room temperature, and the obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (2 mg). 1H-NMR (DMSO-d6) d ppm 5.76 (2H, s), 7.04 (1H, d, J=8.5 Hz), 7.74 (1H, dd, J=8.5, 2.3 Hz), 8.20-8.28 (2H, m), 8.62-8.81 (3H, m), 9.38-9.85 (2H, m).
  • 16
  • [ 58483-97-9 ]
  • [ 421552-12-7 ]
  • [ 1021873-77-7 ]
YieldReaction ConditionsOperation in experiment
Example 189 5-chloro-1-(2-cyano-5-fluorobenzyl)-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added <strong>[421552-12-7]2-(bromomethyl)-4-fluorobenzonitrile</strong> (0.29 g), and the mixture was stirred at 100C for 14 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=3:2 - 19:1). 2N Hydrochloric acid-methanol solution (1 ml) was added to the obtained yellow oil at room temperature, and the obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (34 mg). 1H-NMR (DMSO-d6) d ppm 5.76 (2H, s), 7.07 (1H, dd, J=9.6, 2.3 Hz), 7.40-7.51 (1H, m), 8.12 (1H, dd, J=8.7, 5.5 Hz), 8.23 (1H, s), 8.58-8.77 (3H, m), 9.40-9.81 (2H, m).
  • 17
  • [ 13438-65-8 ]
  • [ 58483-97-9 ]
YieldReaction ConditionsOperation in experiment
(Step 1) To a solution of <strong>[13438-65-8]2-aminonicotinamide</strong> (0.5 g) in concentrated hydrochloric acid (3 ml) was added dropwise 30% aqueous hydrogen peroxide (0.3 ml). After stirring at 60C for 1 hr, the reaction mixture was diluted with water and basified with 1N aqueous sodium hydroxide solution. The mixture was extracted with a mixed solution of ethyl acetate and THF, washed with saturated brine and dried over magnesium sulfate. The reaction solvent was concentrated under reduced pressure, and the residue was purified by silica gel chromatography (ethyl acetate) to give 2-amino-5-chloronicotinamide as crystals (0.25 g). 1H-NMR (DMSO-d6) d ppm 7.36 (2 H, s) 7.46 (1 H, s) 7.99 - 8.07 (2 H, m) 8.10 (1 H, d, J=2.65 Hz).
  • 18
  • [ 17515-77-4 ]
  • [ 58483-97-9 ]
  • [ 1021896-50-3 ]
YieldReaction ConditionsOperation in experiment
Example 153 5-chloro-2-imino-1-[5-(trifluoromethyl)-2-furyl]methyl}-1,2-dihydropyridine-3-carboxamide hydrochloride To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added <strong>[17515-77-4]2-(bromomethyl)-5-(trifluoromethyl)furan</strong> (0.30 g), and the mixture was stirred at 100C for 4 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate. The obtained crystals were dissolved in aqueous sodium hydrogen carbonate solution, and the mixture was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was treated by silica gel chromatography (ethyl acetate 100%?ethyl acetate:methanol=5:1) to give a yellow solid.
  • 19
  • [ 58483-97-9 ]
  • [ 1021871-33-9 ]
  • [ 1021873-47-1 ]
YieldReaction ConditionsOperation in experiment
30% In N,N-dimethyl-formamide at 100℃; for 3h;
In N,N-dimethyl-formamide at 100℃; for 3h; 159.3 (Step 3) To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 3-(bromomethyl)-5-chlorobenzamide (0.26 g) obtained in Step 2, and the mixture was stirred at 100°C for 3 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (110 mg). 1H-NMR (DMSO-d6) d ppm 5.57 (2 H, s) 7.61 (2 H, s) 7.67 (1 H, s) 7.94 (1 H, s) 8.14 (1 H, s) 8.20 (1 H, s) 8.59 (1 H, s) 8.63 (1 H, d, J=1.51 Hz) 8.81 (1 H, d, J=1.14 Hz) 9.42 (2 H, s).
  • 20
  • [ 853368-35-1 ]
  • [ 58483-97-9 ]
  • [ 1021873-78-8 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 14h; 181.4 (Step 4) To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 3-(bromomethyl)-5-fluorobenzonitrile (0.29 g) obtained in Step 3, and the mixture was stirred at 100°C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (69 mg). 1H-NMR (DMSO-d6) d ppm 5.58 (2H, s), 7.60-7.67 (1H, m), 7.69 (1H, s), 7.86-7.95 (1H, m), 8.21 (1H, s), 8.59 (1H, s), 8.64 (1H, d, J= 2.1 Hz), 8.75 (1H, d, J= 2.1 Hz), 9.44 (2H, br-s).
  • 21
  • [ 1021871-36-2 ]
  • [ 58483-97-9 ]
  • [ 1021873-81-3 ]
YieldReaction ConditionsOperation in experiment
23% In N,N-dimethyl-formamide at 100℃; for 3h;
In N,N-dimethyl-formamide at 100℃; for 14h; 182.4 (Step 4) To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 3-(bromomethyl)-5-chlorobenzonitrile (0.29 g) obtained in Step 3, and the mixture was stirred at 100°C for 14 hr. The reaction mixture was diluted with ethyl acetate. The precipitate was collected by filtration and washed with ethyl acetate. The obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (80 mg). 1H-NMR (DMSO-d6) d ppm 5.56 (2H, s), 7.74-7.80 (1H, m), 7.81-7.88 (1H, m), 8.02-8.14 (1H, m), 8.21 (1H, s), 8.53-8.70 (2H, m), 8.71-8.8.1 (1H, m), 9.21-9.66 (2H, m).
  • 22
  • [ 1021871-37-3 ]
  • [ 58483-97-9 ]
  • [ 1021873-83-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 3-(bromomethyl)-4-chlorobenzonitrile; 2-amino-5-chloropyridine-3-carboxamide In N,N-dimethyl-formamide at 100℃; for 14h; Stage #2: With water; sodium hydrogencarbonate Stage #3: With hydrogenchloride In methanol 188.2 (Step 2) To a solution of 2-amino-5-chloronicotinamide (0.15 g) in N,N-dimethylformamide (3 ml) was added 3-(bromomethyl)-4-chlorobenzonitrile (0.31 g), and the mixture was stirred at 100°C for 14 hr. The reaction mixture was quenched with saturated aqueous sodium hydrogen carbonate solution and extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure, and the obtained residue was purified by silica gel chromatography (ethyl acetate:hexane=3:2 - 19:1). 2N Hydrochloric acid-methanol solution (1 ml) was added to the obtained yellow oil at room temperature, and the obtained precipitate was recrystallized from methanol-ethyl acetate to give the title compound (43 mg). 1H-NMR (DMSO-d6) d ppm 5.65 (2H, s), 7.41 (1H, dd, J=8.2, 1.5 Hz), 7.78 (1H, d, J=1.5 Hz), 8.02 (1H, d, J= 8.2 Hz), 8.21 (1H, s), 8.61-8.71 (2H, m), 8.78 (1H, d, J=2.1 Hz), 9.37-9.69 (2H, m).
  • 23
  • [ 254897-02-4 ]
  • [ 58483-97-9 ]
  • [ 1192347-85-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 1-bromo-4-(bromomethyl)-2-(methylsulfonyl)benzene; 2-amino-5-chloropyridine-3-carboxamide In N,N-dimethyl-formamide at 90℃; for 24h; Stage #2: With hydrogenchloride In methanol; ethyl acetate 19 Example 19 1-[4-bromo-3-(methylsulfonyl)benzyl]-5-chloro-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride A solution of 2-amino-5-chloronicotinamide (373 mg) and 1-bromo-4-(bromomethyl)-2-(methylsulfonyl)benzene (1.07 g) in DMF (5 ml) was stirred at 90° C. for 24 hr. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in 1N sodium hydroxide solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=4:1). The obtained yellow solid was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (2 ml) was added, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (310 mg). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.40 (3H, s), 5.62 (2H, s), 7.49 (1H, dd, J=8.29, 2.26 Hz), 7.95 (1H, d, J=8.10 Hz), 8.14 (1H, d, J=2.26 Hz), 8.21 (1H, s) 8.57-8.71 (2H, m), 8.84 (1H, d, J=2.07 Hz), 9.52 (2H, s).
  • 24
  • [ 145908-29-8 ]
  • [ 58483-97-9 ]
  • [ 1192348-24-5 ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide; at 90℃; (Step 3) A solution of 2-amino-5-chloronicotinamide (202 mg) and <strong>[145908-29-8]methyl 4-chloro-2-bromomethylbenzoate</strong> obtained in Step 2 (470 mg) in DMF (5 ml) was stirred overnight at 90 C. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were recrystallized from ethanol and ethyl acetate to give the title compound (78 mg). 1H NMR (300 MHz, DMSO-d6) delta ppm 3.90 (3H, s) 5.79 (2H, s) 6.92 (1H, d, J=1.9 Hz) 7.63 (1H, dd, J=1.9, 8.5 Hz) 8.08 (1H, d, J=8.5 Hz) 8.21 (1H, s) 8.52-8.72 (3H, m) 9.12-9.78 (2H, m).
  • 25
  • [ 694481-02-2 ]
  • [ 58483-97-9 ]
  • [ 1192347-48-0 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 4-(bromomethyl)-2-chloro-1-(methylsulfonyl)benzene; 2-amino-5-chloropyridine-3-carboxamide In N,N-dimethyl-formamide at 100℃; for 4h; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride In methanol; ethyl acetate 3 Example 3 5-chloro-1-[3-chloro-4-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride A solution of 2-amino-5-chloronicotinamide (200 mg) and 4-(bromomethyl)-2-chloro-1-(methylsulfonyl)benzene (430 mg) in DMF (3 ml) was stirred at 100° C. for 4 hr. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in 1N sodium hydroxide solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=9:1→1:0). The obtained yellow solid was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution was added, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (65 mg). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.38 (3H, s), 5.68 (2H, s), 7.45 (1H, d), 7.78 (1H, d, J=1.13 Hz), 8.04 (1H, d, J=8.29 Hz), 8.22 (1H, s), 8.58-8.73 (2H, m), 8.82 (1H, d, J=1.32 Hz), 9.55 (2H, s).
  • 26
  • [ 694481-13-5 ]
  • [ 58483-97-9 ]
  • [ 1192347-51-5 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-bromo-4-(bromomethyl)-1-(methylsulfonyl)benzene; 2-amino-5-chloropyridine-3-carboxamide In N,N-dimethyl-formamide at 100℃; for 6h; Stage #2: With sodium hydroxide In water Stage #3: With hydrogenchloride In methanol; ethyl acetate 6 Example 6 1-[3-bromo-4-(methylsulfonyl)benzyl]-5-chloro-2-imino-1,2-dihydropyridine-3-carboxamide hydrochloride A solution of 2-amino-5-chloronicotinamide (300 mg) and 2-bromo-4-(bromomethyl)-1-(methylsulfonyl)benzene (860 mg) in DMF (5 ml) was stirred at 100° C. for 6 hr. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in 1N sodium hydroxide solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=9:1→ethyl acetate:methanol=9:1). The obtained yellow solid was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution was added, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (195 mg). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.38 (3H, s), 5.66 (2H, s), 7.47 (1H, d, J=8.33 Hz), 7.95 (1H, s), 8.06 (1H, d, J=8.33 Hz), 8.22 (1H, s), 8.67 (2H, s), 8.82 (1H, s), 9.53 (2H, s).
  • 27
  • [ 58483-97-9 ]
  • [ 1192347-45-7 ]
  • [ 1192347-42-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-5-chloropyridine-3-carboxamide; 2-(bromomethyl)-4-chloro-1-(methylsulfonyl)benzene In N,N-dimethyl-formamide at 100℃; for 3h; Stage #2: With sodium hydrogencarbonate In water Stage #3: With hydrogenchloride In methanol; ethyl acetate 1.4 (Step 4) A solution of 2-amino-5-chloronicotinamide (210 mg) and 2-(bromomethyl)-4-chloro-1-(methylsulfonyl)benzene obtained in Step 3 (450 mg) in DMF (5 ml) was stirred at 100° C. for 3 hr. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in aqueous sodium hydrogen carbonate solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=1:1→3:1). The obtained yellow solid was dissolved in methanol, and 4N hydrogen chloride-ethyl acetate solution was added. The solvent was evaporated under reduced pressure, and the residue was crystallized from methanol-ethyl acetate to give the title compound (30 mg). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.42 (3H, s), 5.84 (2H, s), 7.15 (1H, d, J=1.88 Hz), 7.78 (1H, dd, J=8.48, 1.88 Hz), 8.07 (1H, d, J=8.48 Hz), 8.24 (1H, s), 8.63-8.75 (3H, m), 9.67 (2H, s).
  • 28
  • [ 58483-97-9 ]
  • [ 1192347-77-5 ]
  • [ 1192347-76-4 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-5-chloropyridine-3-carboxamide; 4-(bromomethyl)-1-chloro-2-(methylsulfonyl)benzene In N,N-dimethyl-formamide at 90℃; for 20h; Stage #2: With hydrogenchloride In methanol; ethyl acetate 15.2 (Step 2) A solution of 2-amino-5-chloronicotinamide (484 mg) and 4-(bromomethyl)-1-chloro-2-(methylsulfonyl)benzene obtained in Step 1 (1.2 g) in DMF (10 ml) was stirred at 90° C. for 20 hr. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in 1N sodium hydroxide solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate). The obtained yellow solid was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (2 ml) was added, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (160 mg). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.39 (3H, s), 5.63 (2H, s), 7.60 (1H, dd, J=8.29, 2.26 Hz), 7.79 (1H, d, J=8.29 Hz), 8.12 (1H, d, J=2.26 Hz), 8.20 (1H, s), 8.61 (1H, s), 8.63 (1H, d, J=2.26 Hz), 8.83 (1H, d, J=2.26 Hz), 9.49 (2H, s).
  • 29
  • [ 58483-97-9 ]
  • [ 1192347-88-8 ]
  • [ 1192347-86-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-5-chloropyridine-3-carboxamide; 4-(bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene In N,N-dimethyl-formamide at 90℃; for 24h; Stage #2: With hydrogenchloride In methanol; ethyl acetate 20.2 (Step 2) A solution of 2-amino-5-chloronicotinamide (685 mg) and 4-(bromomethyl)-1-fluoro-2-(methylsulfonyl)benzene obtained in Step 1 (1.6 g) in DMF (10 ml) was stirred at 90° C. for 24 hr. The mixture was allowed to cool to room temperature, methanol and ethyl acetate were added, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in 1N sodium hydroxide solution, and the solution was extracted with ethyl acetate. The organic layer was washed with saturated brine, and dried over magnesium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=4:1). The obtained yellow solid was dissolved in methanol, 4N hydrogen chloride-ethyl acetate solution (2 ml) was added, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (510 mg). 1H NMR (300 MHz, DMSO-d6) δ ppm 3.36 (3H, s), 5.62 (2H, s), 7.51-7.65 (1H, m), 7.67-7.78 (1H, m), 7.98 (1H, dd, J=6.44, 2.27 Hz), 8.21 (1H, s), 8.64 (2H, d, J=2.27 Hz), 8.85 (1H, d, J=2.27 Hz), 9.53 (2H, s).
  • 30
  • [ 58483-97-9 ]
  • [ 1192348-13-2 ]
  • [ 1192348-09-6 ]
YieldReaction ConditionsOperation in experiment
Stage #1: 2-amino-5-chloropyridine-3-carboxamide; 1-(bromomethyl)-2-(cyclopentylsulfonyl)benzene In N,N-dimethyl-formamide at 90℃; for 20h; Stage #2: With hydrogenchloride In methanol; ethyl acetate 27.4 (Step 4) A solution of 2-amino-5-chloronicotinamide (200 mg) and 1-(bromomethyl)-2-(cyclopentylsulfonyl)benzene obtained in Step 3 (530 mg) in DMF (5 ml) was stirred at 90° C. for 20 hr. The mixture was allowed to cool to room temperature, ethyl acetate was added, and the precipitated crystals were collected by filtration. The obtained crystals were dissolved in aqueous sodium hydrogen carbonate solution, and the solution was extracted with a mixed solvent of ethyl acetate-tetrahydrofuran. The organic layer was washed with saturated brine, dried over magnesium sulfate, and filtered. The solvent was evaporated under reduced pressure. The residue was purified by basic silica gel column chromatography (ethyl acetate:hexane=3:1). The obtained residue was dissolved in methanol, and 4N hydrogen chloride-ethyl acetate solution (0.5 ml) was added. The mixture was crystallized from methanol-ethyl acetate, and the precipitated crystals were collected by filtration, and recrystallized to give the title compound (70 mg). 1H NMR (300 MHz, DMSO-d6) δ ppm 1.46-2.05 (8H, m) 3.98-4.20 (1H, m) 5.84 (2H, s) 6.98-7.08 (1H, m) 7.61-7.76 (2H, m) 7.95-8.08 (1H, m) 8.25 (1H, s) 8.63 (1H, d, J=1.88 Hz) 8.65-8.75 (2H, m) 9.60 (2H, s).
  • 31
  • [ 26163-03-1 ]
  • [ 58483-97-9 ]
  • 32
  • [ 58483-97-9 ]
  • 5-chloro-2-aminonicotinic acid 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: dihydrogen peroxide; methyltrioxorhenium(VII) / water; ethanol / 3 h / 20 °C 2.1: potassium hydroxide / water / 3 h / Reflux 2.2: 0 °C / pH 4 - 5
  • 33
  • [ 58483-97-9 ]
  • 5-chloro-2-aminonicotinamide 1-oxide [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% With dihydrogen peroxide; methyltrioxorhenium(VII) In ethanol; water at 20℃; for 3h;
  • 34
  • [ 58483-97-9 ]
  • [ 958360-30-0 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1,4-dioxane / 12 h / 120 °C 2: P,P-dichlorophenylphosphine oxide / 6 h / 180 °C
Multi-step reaction with 2 steps 1: 1,4-dioxane / 12 h / 120 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 130 °C / Inert atmosphere
  • 35
  • [ 58483-97-9 ]
  • 2,6-dichloropyrido[2,3-d]pyrimidin-4-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1,4-dioxane / 12 h / 120 °C 2: P,P-dichlorophenylphosphine oxide / 6 h / 180 °C 3: sodium hydroxide / water; butan-1-ol / 2 h / 20 °C
  • 36
  • [ 58483-97-9 ]
  • 6-chloro-2-(4-methylpiperazin-1-yl)pyrido[2,3-d]pyrimidin-4(3H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1,4-dioxane / 12 h / 120 °C 2: P,P-dichlorophenylphosphine oxide / 6 h / 180 °C 3: sodium hydroxide / water; butan-1-ol / 2 h / 20 °C 4: ethanol / 1 h / 80 °C
  • 37
  • [ 58483-97-9 ]
  • 4,6-dichloro-2-(4-methylpiperazin-1-yl)pyrido[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1,4-dioxane / 12 h / 120 °C 2: P,P-dichlorophenylphosphine oxide / 6 h / 180 °C 3: sodium hydroxide / water; butan-1-ol / 2 h / 20 °C 4: ethanol / 1 h / 80 °C 5: trichlorophosphate / 12 h / 90 °C
  • 38
  • [ 58483-97-9 ]
  • 6-chloro-4-hydrazinyl-2-(4-methylpiperazin-1-yl)pyrido[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 6 steps 1: 1,4-dioxane / 12 h / 120 °C 2: P,P-dichlorophenylphosphine oxide / 6 h / 180 °C 3: sodium hydroxide / water; butan-1-ol / 2 h / 20 °C 4: ethanol / 1 h / 80 °C 5: trichlorophosphate / 12 h / 90 °C 6: triethylamine; hydrazine hydrate / ethanol / 1 h / -20 °C
  • 39
  • [ 58483-97-9 ]
  • 9-chloro-5-(4-methylpiperazin-1-yl)pyrido[3,2-e][1,2,4]triazolo[4,3-c]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1: 1,4-dioxane / 12 h / 120 °C 2: P,P-dichlorophenylphosphine oxide / 6 h / 180 °C 3: sodium hydroxide / water; butan-1-ol / 2 h / 20 °C 4: ethanol / 1 h / 80 °C 5: trichlorophosphate / 12 h / 90 °C 6: triethylamine; hydrazine hydrate / ethanol / 1 h / -20 °C 7: 2 h / 100 °C
  • 40
  • [ 58483-97-9 ]
  • [ 503-38-8 ]
  • [ 56783-83-6 ]
YieldReaction ConditionsOperation in experiment
84% In 1,4-dioxane at 120℃; for 12h; 42.a Synthesis of 6-chloropyrido[2,3-d]pyrimidin-2,4(1H,3H)-dione The mixture of 2-amino-5-chloronicotineamide (169.0 mg, 0.98 mmol) and diphosgene (646.0 mg, 3.14 mmol) dissolved in 1,4-dioxane (10.0 mL) was stirred at 120° C. for 12 hours and then cooled to room temperature. Et2O was added thereto to form a solid, and the formed solid was filtered and then dried under reduced pressure to obtain ivory solid compound of 6-chloropyrido[2,3-d]pyrimidin-2,4(1H,3H)-dione (163.0 mg, 84%). [0692] 1H-NMR (300 MHz, DMSO-d6); δ: 11.59 (s, 2H), 8.60 (d, 1H, J=2.8 Hz), 8.19 (d, 1H, J=2.6 Hz)
71% In 1,4-dioxane at 120℃; for 12h; Inert atmosphere; 3.1.9. 6-Chloropyrido[2,3-d]pyrimidine-2,4(1H,3H)-dione (20) To a solution of 2-amino-5-chloronicotinamide 19 (34.97 mmol) in 1,4-dioxane (30 mL) was addeddiphosgene (111.90 mmol), then the mixture was charged with N2 and stirred at 120 C for 12 h.After completion (monitored by TLC), cooled to r.t. Dry diethyl ether (100 mL) was added and stirredat r.t for 1 h, the precipitation separated out. Suction and drying to give a brown solid. Yield 71%,m.p. >250 C. 1H-NMR (300 MHz, DMSO-d6) (ppm): 11.88 (s, 1H, NH), 11.62 (s, 1H, NH), 8.66 (d,J = 2.6 Hz, 1H, ArH), 8.26 (d, J = 2.5 Hz, 1H, ArH).
  • 41
  • [ 58483-97-9 ]
  • 4-(bromomethyl)-2-chlorobenzamide [ No CAS ]
  • 1-(4-carbamoyl-3-chlorobenzyl)-5-chloro-2-imino-1,2-dihydropyridine-3-carboxamide monohydrobromide [ No CAS ]
YieldReaction ConditionsOperation in experiment
30% In N,N-dimethyl-formamide at 100℃; for 3h;
  • 43
  • [ 694481-02-2 ]
  • [ 58483-97-9 ]
  • 5-chloro-1-[3-chloro-4-(methylsulfonyl)benzyl]-2-imino-1,2-dihydropyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
In N,N-dimethyl-formamide at 100℃; for 3h;
  • 45
  • [ 24517-64-4 ]
  • [ 58483-97-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sulfuric acid / 5 h / 100 °C 2: hydrogenchloride; dihydrogen peroxide / water / 1 h / 0 - 60 °C
  • 47
  • [ 5345-47-1 ]
  • [ 58483-97-9 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; ammonium chloride / N,N-dimethyl-formamide / 12 h / 20 °C 2: hydrogenchloride; dihydrogen peroxide / 6 h / 60 °C
  • 48
  • [ 58483-97-9 ]
  • 2,6-dichloropyrido[2,3-d]pyrimidine [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: 1,4-dioxane / 12 h / 120 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 130 °C / Inert atmosphere 3: tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) / toluene / 1 h / 100 °C / Inert atmosphere
  • 49
  • [ 58483-97-9 ]
  • 1-(6-chloropyrido[2,3-d]pyrimidin-2-yl)-3-cyclopentylurea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: 1,4-dioxane / 12 h / 120 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 130 °C / Inert atmosphere 3: tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) / toluene / 1 h / 100 °C / Inert atmosphere 4: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; potassium <i>tert</i>-butylate / 2 h / 60 °C / Inert atmosphere
  • 50
  • [ 58483-97-9 ]
  • 1-cyclopentyl-3-(6-(1-methyl-1H-pyrazol-4-yl)pyrido[2,3-d]pyrimidin-2-yl)urea [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: 1,4-dioxane / 12 h / 120 °C / Inert atmosphere 2: N-ethyl-N,N-diisopropylamine; trichlorophosphate / 12 h / 130 °C / Inert atmosphere 3: tri-n-butyl-tin hydride; tetrakis(triphenylphosphine) palladium(0) / toluene / 1 h / 100 °C / Inert atmosphere 4: 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; palladium diacetate; potassium <i>tert</i>-butylate / 2 h / 60 °C / Inert atmosphere 5: potassium carbonate; (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride / 1,4-dioxane; water / 60 °C / Inert atmosphere
Same Skeleton Products
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