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[ CAS No. 131418-11-6 ]

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Chemical Structure| 131418-11-6
Chemical Structure| 131418-11-6
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Product Details of [ 131418-11-6 ]

CAS No. :131418-11-6 MDL No. :MFCD09862946
Formula : C7H7ClN2O Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :170.60 g/mol Pubchem ID :-
Synonyms :

Safety of [ 131418-11-6 ]

Signal Word:Warning Class:
Precautionary Statements:P305+P351+P338 UN#:
Hazard Statements:H302-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 131418-11-6 ]

  • Downstream synthetic route of [ 131418-11-6 ]

[ 131418-11-6 ] Synthesis Path-Downstream   1~7

  • 1
  • [ 6313-54-8 ]
  • [ 79-37-8 ]
  • [ 131418-11-6 ]
YieldReaction ConditionsOperation in experiment
With methylamine In tetrahydrofuran; ethanol; N,N-dimethyl-formamide 2-Chloro-N-methyl-isonicotinamide (8-2) 2-Chloro-N-methyl-isonicotinamide (8-2) 2-Chloro-isonicotinic acid (12-1, 5.15 g, 32.7 mmol) was stirred in 65 mL anhydrous THF under N2. The reaction (not homogeneous) was cooled to 0° C. and oxalyl chloride (2.85 mL, 32.7 mmol) was added, followed by addition of 1 drop anhydrous DMF. Slight bubbling occurred. The reaction was allowed to warm to room temperature. After 4 hours reaction is homogeneous and after a total of 5 hours the reaction was quickly added by pipette to a solution of methylamine (7.11 g, 228 mmol) in EtOH (20 mL). The resulting solution was concentrated in vacuo and diluted with saturated NaHCO3 (aq). The solution was extracted 3* with EtOAc and the organic extracts were dried over Na2SO4, filtered ands concentrated to provide the titled compound. 1H NMR (CDCl3) δ 8.50 (d, 1H, J=5.1 Hz), 7.66 (s, 1H), 7.53 (d, 1H, J=5.1 Hz), 6.36 (bs, 1H), 3.04 (d, 2H, J=5.0 Hz).
With methylamine In tetrahydrofuran; ethanol 2-Chloro-N-methyl-isonicotinamide (12-2) 2-Chloro-N-methyl-isonicotinamide (12-2) 2-Chloro-isonicotinic acid (12-1, 5.15 g, 32.7 mmol) was stirred in 65 mL anhydrous THF under N2. The reaction (not homogeneous) was cooled to 0° C. and oxalyl chloride (2.85 mL, 32.7 mmol) was added, followed by addition of 1 drop anh DMF. Slight bubbling occurs. The reaction was allowed to warm to RT. After 4 h reaction is homogeneous and after a total of 5 h the reaction was quickly added by pipet to a solution of methylamine (7.11 g, 228 mmol) in EtOH (20 mL). The resulting solution was concentrated in vacuo and diluted with sat NaHCO3 (aq). The solution was extracted 3* with EtOAc and the organic extracts were dried over Na2SO4, filtered ands concentrated to provide the titled compound. 1H NMR (CDCl3) δ 8.50 (d, 1H, J=5.1 Hz), 7.66 (s, 1H), 7.53 (d, 1H, J=5.1 Hz), 6.36 (bs, 1H), 3.04 (d, 2H, J=5.0 Hz).
  • 2
  • [ 131418-11-6 ]
  • 2-chloro-3,N-dimethyl-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With n-butyllithium; methyl iodide In tetrahydrofuran; hexane 2-Chloro-3,N-dimethyl-isonicotinamide (8-3) 2-Chloro-3,N-dimethyl-isonicotinamide (8-3) 2-Chloro-N-methyl-isonicotinamide (8-2, 1.03 g, 6.04 mmol) was dissolved in 12 mL anhydrous THF and the resulting solution was cooled to -78° C. nBuLi (1.6 M in hexane, 7.55 mL, 12.1 mmol) was added slowly. After 20 minutes MeI (0.375 mL, 6.04 mmol) was added slowly. Approximately halfway through the addition a brown gum quickly formed in the mixture. The remainder of the MeI was added and the reaction was allowed to warm to 0° C. and then to room temperature. After 30 minutes at room temperature the reaction was quenched with water. The mixture was extracted 3* with EtOAc, and the organic extracts were dried over Na2SO4, filtered, and concentrated. 1H NMR showed 2:1:1 monomethylated 8-3:dimethylated:starting material. Purification by flash column chromatography (98:2 DCM/MeOH) afforded a 2:1 mixture of the titled compound and 2-chloro-3,N-dimethyl-isonicotinamide.
With n-butyllithium; methyl iodide In tetrahydrofuran; hexane 2-Chloro-3,N-dimethyl-isonicotinamide (12-3) 2-Chloro-3,N-dimethyl-isonicotinamide (12-3) 2-Chloro-N-methyl-isonicotinamide (12-2, 1.03 g, 6.04 mmol) was dissolved in 12 mL anhydrous THF and the resulting solution was cooled to -78° C. nBuLi (1.6 M in hexane, 7.55 mL, 12.1 mmol) was added slowly. After 20 min MeI (0.375 mL, 6.04 mmol) was added slowly. Approximately halfway through the addition a brown gum quickly formed in the mixture. The remainder of the MeI was added and the reaction was allowed to warm to 0° C. and then to RT. After 30 min at RT the reaction was quenched with water. The mixture was extracted 3* with EtOAc, and the organic extracts were dried over Na2SO4, filtered, and concentrated. 1H NMR shows 2:1:1 desired:dimethylated pdt:starting material. Purify by flash column chromatography (98:2 DCM/MeOH) afforded a 2:1 mixture of the titled compound and 2-chloro-3,N-dimethyl-isonicotinamide.
  • 3
  • [ 131418-11-6 ]
  • 2,3-Dichloro-N-methyl-isonicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
With N-chloro-succinimide; diisopropylamine In tetrahydrofuran 2,3-Dichloro-N-methyl-isonicotinamide (13-1) 2,3-Dichloro-N-methyl-isonicotinamide (13-1) 2-Chloro-N-methyl-isonicotinamide (12-2, 1.19 g, 6.98 mmol) was dissolved in 2 mL anhydrous THF and the solutin was cooled to -78° C. LDA (2M, 7.33 mL, 14.7 mmol) was added dropwise and the reaction turns orange. After 15 min NCS (1.02 g, 7.67 mmol) was added and the reaction was allowed to warm to RT. After 1 h at RT HPLC shows "3:1 starting material/product. The reaction was quenched with water, extracted 3* w/EtOAc, and the organic phases were dried over Na2SO4, filtered, and concentrated. The residue was purified by preparative reverse phase HPLC to afford the pure titled compound. 1H NMR (CDCl3) δ 8.36 (d, 1H, J=4.8 Hz), 7.41 (d, 1H, J=4.8 Hz), 6.10 (bs, 1H), 3.05 (d, 3H, J=4.9 Hz).
  • 4
  • [ 131418-11-6 ]
  • 3-amino-7-bromo-5-(dicyclopropylmethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one [ No CAS ]
  • 2-(3-amino-5-(dicyclopropylmethyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-7-yl)-N-methylisonicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
63mg Stage #1: 3-amino-7-bromo-5-(dicyclopropylmethyl)-1,5-dihydro-4H-pyrazolo[4,3-c]pyridin-4-one With tetrakis(triphenylphosphine) palladium(0); potassium acetate; bis(pinacol)diborane In N,N-dimethyl acetamide at 110℃; for 4h; Inert atmosphere; Stage #2: 2-chloro-N-methylisonicotinamide With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In N,N-dimethyl acetamide; water at 130℃; for 5h; Inert atmosphere; 4 2-(3-amino-5-(dicyclopropylmethyl)-4-oxo-4,5-dihydro-1H-pyrazolo[4,3-c]pyridin-7-yl)-N-methylisonicotinamide Example 1 step obtained in C 3- amino-7-bromo-5- (di-cyclopropylmethyl) -1,5-dihydro -4H- pyrazolo [4,3-c] pyridin-4-one (150 mg), 4,4,4 ', 4', 5,5,5 ', 5'- octamethyl-2,2'-bi (1,3,2-dioxaborolane) (141 mg), tetrakis (triphenylphosphine ) palladium (0) (54 mg), potassium acetate (91 mg) and N, a mixture of N- dimethylacetamide (4 mL), under an argon atmosphere and stirred for 4 hours at 110 ° C..The reaction mixture was cooled to room temperature, 2-chloro -N- methyl-isonicotinamide (95 mg), aqueous sodium carbonate (2 M, 0.464 mL) and tetrakis (triphenylphosphine) palladium (0) (54 mg) was added It was. Under an argon atmosphere, the reaction mixture was stirred for 5 hours at 130. ° C..After the reaction mixture was cooled to room temperature, water was added, and the mixture was extracted with ethyl acetate. The extract was washed with water and brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel chromatography (NH, methanol / ethyl acetate). The residue to give the title compound solidified from methanol (63 mg).
  • 5
  • [ 65287-34-5 ]
  • [ 74-89-5 ]
  • [ 131418-11-6 ]
YieldReaction ConditionsOperation in experiment
1.52 g With triethylamine In dichloromethane at 20℃; for 0.5h; 33 2-Chloro-N-methylisonicotinamide (33.3) To a mixture of TEA (1.52 mg, 15 mmol) and methanamine (372 mg, 12 mmol) in DCM (20 mL) was added 2-chloroisonicotinoyl chloride (1.76 g, 10 mmol), the mixture was stirred at r.t. for 0.5 h. To the mixture was added H2O (50 mL), extracted with DCM (20 mL x 2). The combined organic layer was washed with brine (50 mL x 3), dried over Na2SO4, filtered, concentrated in vacuo and purified via pre-TLC (Petroleum ether / EtOAc= 2 / 1) to give 2-chloro- N-methylisonicotinamide (1.52 g, 89.4 % yield) as a white solid. LC/MS (ESI, m/z): [M +1]+ = 171.0.
  • 6
  • [ 6313-54-8 ]
  • [ 131418-11-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide; oxalyl dichloride / dichloromethane / 1 h / Reflux 2: triethylamine / dichloromethane / 0.5 h / 20 °C
  • 7
  • [ 131418-11-6 ]
  • 2-mercapto-N-methylisonicotinamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
47.6% With sodium hydrogen sulfide In N,N-dimethyl-formamide at 130℃; 33 2-Mercapto-N-methylisonicotinamide To a mixture of 2-chloro-N-methylison co namide (340 mg, 2 mmol) in DMF (5 mL) was added NaSH (224 mg, 4 mmol), the mixture was stirred at 130oC for overnight. To the residue was added H2O (10 mL), extracted with EtOAc (10 mL x 2). The combined organic layer was washed with brine (50 mL x 3), dried over Na2SO4, filtered, concentrated in vacuo and purified via pre-TLC (DCM / MeOH = 40 / 1) to give 2-mercapto-N-methylisonicotinamide (160 mg, 47.6 % yield) as a yellow solid. LC/MS (ESI, m/z): [M +1]+ = 169.0.
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