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[ CAS No. 859538-41-3 ]

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Chemical Structure| 859538-41-3
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Product Details of [ 859538-41-3 ]

CAS No. :859538-41-3 MDL No. :MFCD18256209
Formula : C7H5F2NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :MKLFNFRBDNMKIU-UHFFFAOYSA-N
M.W :173.12 Pubchem ID :23145481
Synonyms :

Safety of [ 859538-41-3 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P312-P362-P403+P233-P501 UN#:
Hazard Statements:H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 859538-41-3 ]

* 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 [ 859538-41-3 ]

[ 859538-41-3 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 1221272-81-6 ]
  • [ 859538-41-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1.1: triethylamine / 1,3-bis-(diphenylphosphino)propane; palladium diacetate / dimethyl sulfoxide / 24 h / 60 °C / 31029.7 Torr 2.1: sodium hydroxide / ethanol / 5 h / 0 - 20 °C 2.2: pH 4
Multi-step reaction with 2 steps 1.1: triethylamine / 1,3-bis-(diphenylphosphino)propane; palladium diacetate / dimethyl sulfoxide / 24 h / 60 °C / 31029.7 Torr / autoclave 2.1: lithium hydroxide / ethanol / 5 h / 0 - 20 °C 2.2: pH ~ 4
  • 2
  • [ 1346148-42-2 ]
  • [ 859538-41-3 ]
YieldReaction ConditionsOperation in experiment
62% Stage #1: 5-difluoromethyl-pyridine-2-carboxylic acid methyl ester With lithium hydroxide In ethanol at 0 - 20℃; for 5h; Stage #2: With citric acid In water 108.b A solution of 5-difluoromethyl-pyridine-2-carboxylic acid methyl ester (700 mg, 3.7 mmol) in ethanol (8.0 ml) was treated with a solution of sodium hydroxide (5M, 1.5 ml) at 0 °C. Then the reaction mixture was allowed to attain room temperature and was stirred for 5 hours. For the workup, ethanol was removed at reduced pressure. The resulting solid was dissolved in water (5 ml) and the solution was washed with ethyl acetate (2 x 5 ml). The aqueous layer acidified with a solution of citric acid (10%, pH~4), followed by extraction with a 7:3-mixture of dichloromethane and methanol (5 x 10 ml). The combined organic layers were washed with brine (20 ml), dried over sodium sulphate, and evaporated at reduced pressure. The 5- difluoromethyl-pyridine-2-carboxylic acid was obtained as a white solid (400 mg, 62%> of theory).
62% Stage #1: 5-difluoromethyl-pyridine-2-carboxylic acid methyl ester With sodium hydroxide In ethanol at 0 - 20℃; for 5h; Stage #2: With citric acid In water 108.b b) 5-Difluoromethyl-pyridine-2-carboxylic acidA solution of 5-difluoromethyl-pyridine-2-carboxylic acid methyl ester (700 mg, 3.7 mmol) in ethanol (8.0 ml) was treated with a solution of sodium hydroxide (5M, 1.5 ml) at 0° C. Then the reaction mixture was allowed to attain room temperature and was stirred for 5 hours. For the workup, ethanol was removed at reduced pressure. The resulting solid was dissolved in water (5 ml) and the solution was washed with ethyl acetate (2×5 ml). The aqueous layer acidified with a solution of citric acid (10%, pH4), followed by extraction with a 7:3-mixture of dichloromethane and methanol (5×10 ml). The combined organic layers were washed with brine (20 ml), dried over sodium sulphate, and evaporated at reduced pressure. The 5-difluoromethyl-pyridine-2-carboxylic acid was obtained as a white solid (400 mg, 62% of theory).
  • 4
  • [ 149806-06-4 ]
  • [ 859538-41-3 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide; ethyl acetate; n-heptane 2: n-heptane; toluene 3: hydrogenchloride / liquid HCl
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1.5 h / 120 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 °C 3: hydrogenchloride; water / 1.5 h / 110 °C
Multi-step reaction with 3 steps 1: ethyl acetate; N,N-dimethyl-formamide; n-heptane 2: toluene; n-heptane 3: hydrogenchloride / liquid HCl
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1.5 h / 120 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 °C 3: hydrogenchloride / water / 15 h / 110 °C
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1.5 h / 120 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 °C 3: hydrogenchloride; water / 1.5 h / 110 °C
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 3 h / 120 °C / Inert atmosphere 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 16 h / 25 °C 3: hydrogenchloride; water / 2.5 h / 110 °C
Multi-step reaction with 3 steps 1: N,N-dimethyl-formamide / 1.5 h / 120 °C 2: (bis-(2-methoxyethyl)amino)sulfur trufluoride / toluene / 20 °C 3: hydrogenchloride / water / 1.5 h / 110 °C

  • 6
  • [ 1211540-57-6 ]
  • [ 859538-41-3 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride; water at 110℃; for 1.5h; 16.3 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl)picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110° C. for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z=174 (M+H)
100% With hydrogenchloride; water at 110℃; for 1.5h; 26.3 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl)picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110° C. for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z=174 (M+H).
100% With hydrogenchloride In water at 110℃; for 1.5h; 3 Step 3: 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl) picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110°C for 1.5 h. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z = 174 (M+H) +.
In hydrogenchloride liquid HCl; 16.3 Step 3: Step 3: 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl)picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110° C. for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z=174 (M+H).
In hydrogenchloride liquid HCl; 240.3 Step 3: Step 3: 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl)picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110° C. for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESI+) m/z=174 (M+H).
With hydrogenchloride In water at 110℃; for 15h; 12.3 5-(difluoromethyl)picolinic acid A suspension of 5-(difluoromethyl) picolinonitrile (48 mg, 0.311 mmol) in 12 N aqueous hydrochloric acid (4.3 mL, 140 mmol) was stirred at 110°C for 1.5 hours. After cooling to ambient temperature, the reaction mixture was concentrated and treated with DIPEA (2 mL). The mixture was concentrated and dried in vacuo to provide the title compound in quantitative yield. LC/MS (ESf ) m/z = 174 (M+H) +
With hydrogenchloride; water at 110℃; for 2.5h; 3 Step 3: (0583) 5-(Difluoromethyl)picolinonitrile (118 mg, 0.75 mmol) in 9 mL of conc. HCl was heated at 110° C. for 2.5 h. The mixture was cooled, concentrated and treated with diisopropylethylamine (2 mL). The mixture was re-concentrated and dried in vacuo to give 5-(difluoromethyl)picolinic acid that was used without purification.

  • 7
  • [ 859538-41-3 ]
  • [ 1624604-99-4 ]
YieldReaction ConditionsOperation in experiment
200 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-5-(difluoromethyl)picolinamide Example 200 N-(3-((4S,6S)-2-amino-4-methyl-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4,5-difluorophenyl)-5-(difluoromethyl)picolinamide The title compound was synthesized by procedures and steps analogous to those described in Method Z, Example 186 above, but using 5-(difluoromethyl)picolinic acid (intermediate 12). MS m/z=465.0 [M+H]+. Calculated for C19H15F7N4O2: 464.34 1H NMR (400 MHz, CHLOROFORM-d) δ=9.97 (br. s., 1H), 8.76 (br. s., 1H), 8.38 (d, J=8.2 Hz, 1H), 8.16-8.02 (m, 2H), 7.15 (br. s., 1H), 6.97-6.62 (m, 1H), 4.13-4.00 (m, 1H), 2.80 (d, J=13.7 Hz, 1H), 1.93 (t, J=13.2 Hz, 1H), 1.67 (br. s., 3H)
  • 8
  • [ 859538-41-3 ]
  • [ 1624605-20-4 ]
YieldReaction ConditionsOperation in experiment
221 N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluoro-5-methylphenyl)-5-(difluoromethyl)picolinamide Example 221 N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluoro-5-methylphenyl)-5-(difluoromethyl)picolinamide The title compound was synthesized by procedure and steps analogous to those described in Method A3, Example 216 above, but using 5-(difluoromethyl)picolinic acid (intermediate 12) in step 10. MS m/z=478.9 [M+H]+. Calculated for C20H17F7N4O2: 478.12. 1H NMR (300 MHz, DMSO-d6) δ ppm 1.98 (t, J=12.86 Hz, 1H) 2.26 (d, J=1.90 Hz, 3H) 2.47 (br. s., 1H) 4.28-4.71 (m, 3H) 6.09 (s, 2H) 7.29 (t, J=54.10 Hz, 1H) 7.73 (dd, J=6.65, 2.56 Hz, 1H) 7.82 (dd, J=3.70, 2.80 Hz, 1H) 8.27 (d, J=1.32 Hz, 2H) 8.94 (s, 1H) 10.71 (s, 1H).
  • 9
  • [ 859538-41-3 ]
  • [ 1448793-28-9 ]
YieldReaction ConditionsOperation in experiment
41 Synthesis of N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-(difluoromethyl)picolinamide Example 41 Synthesis of N-(3-((4S,6S)-2-amino-4-(fluoromethyl)-6-(trifluoromethyl)-5,6-dihydro-4H-1,3-oxazin-4-yl)-4-fluorophenyl)-5-(difluoromethyl)picolinamide The title compound was synthesized by procedures and steps analogous to those described in Method F, Example 32 above, but using 5-(difluoromethyl)picolinic acid. MS m/z=464.9 [M+H]+. Calculated for C19H15F7N4O2: 464.11 1H NMR (300 MHz, CHLOROFORM-d) δ ppm 2.29 (t, J=13.30 Hz, 1H) 2.77 (dd, J=13.74, 2.63 Hz, 1H) 4.18-4.32 (m, 1H) 4.41-4.87 (m, 2H) 6.90 (m, J=55.98, 1.00, 1.00 Hz, 1H) 7.16 (dd, J=11.40, 8.92 Hz, 1H) 7.61 (dd, J=6.87, 2.48 Hz, 1H) 8.01-8.15 (m, 2H) 8.39 (d, J=8.04 Hz, 1H) 8.78 (s, 1H) 10.02 (s, 1H).
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