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Chemical Structure| 1446507-68-1 Chemical Structure| 1446507-68-1

Structure of 1446507-68-1

Chemical Structure| 1446507-68-1

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Product Details of [ 1446507-68-1 ]

CAS No. :1446507-68-1
Formula : C15H7ClF6N6
M.W : 420.70
SMILES Code : FC(C1=NC=CC(NC2=NC(Cl)=NC(C3=NC(C(F)(F)F)=CC=C3)=N2)=C1)(F)F
MDL No. :MFCD30607344
InChI Key :SXFBKPOTJNVNEW-UHFFFAOYSA-N
Pubchem ID :89684272

Safety of [ 1446507-68-1 ]

GHS Pictogram:
Signal Word:Warning
Hazard Statements:H315-H319
Precautionary Statements:P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313

Application In Synthesis of [ 1446507-68-1 ]

* 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 [ 1446507-68-1 ]

[ 1446507-68-1 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1446507-68-1 ]
  • [ 2854-16-2 ]
  • [ 1446502-11-9 ]
YieldReaction ConditionsOperation in experiment
96% j0086J To a 15 L glass reactor purged with nitrogen was charged Compound 14 (1.038 kg, 2.47 mol, 1 eq), followed by Me-THF (6.176 kg) and DIEA (0.384 kg, 2.97 mol, 1.2 eq). The resulting mixture was stirred at room temperature and then 1-amino-2-methylpropan-2-ol(0.265 kg, 2.97 mol, 1.2 eq) in Me-THF (2.647 kg) was slowly charged while maintaining 20-30 C. After the reaction was complete, water (2.6 L) and n-heptane (2.076 kg) were added. The mixture was stirred for 20 mm., the aqueous layer was removed, water (2.6 L) was added and the pH of the aqueous phase adjusted to 7 using 0.1N HC1. The aqueous layer was removed, and the organic layer was washed with water (2 x 2.6 L), 4% NaHCO3 (1.1 L), and water (1.15 L). The organic layer was concentrated under vacuum to 3.4 L. Me-THF (4.950 kg) was added, and the mixture was concentrated to 3.4 L. The residue was diluted with Me-THF (4.931 kg). The solution was clarified through a 1.2 t in-line filter. The clarified solution was concentrated to 2.6 L. The residue was heated to 45 C, and then n-heptane (2.599 kg) was added slowly while maintaining 45 C. The batch was seeded with 2-methyl-i -((4-(6-(trifluoromethyl)pyridin-2-yl)- 6-((2-(trifluoromethyl)pyridin-4-yl)amino)- 1,3,5 -triazin-2-yl)amino)propan-2-ol (lOg). nHeptane (2.599 kg) was added slowly while maintaining 45 C. After ih, the batch was cooled down to 20 C. The mixture was stirred at 20 C for ih. The batch was filtered. The solids were washed with n-heptane (2 x 1 L), and then vacuum-dried at 35 C in an oven for 20 h. Isolated yield: 1.124 kg of 2-methyl-i -((4-(6-(trifluoromethyl)pyridin-2-yl)-6-((2- (trifluoromethyl)pyridin-4-yl)amino)- 1,3,5 -triazin-2-yl)amino)propan-2-ol (96 %) as a light yellow powder.
With sodium hydrogencarbonate; In tetrahydrofuran;Reflux; To a solution of 4-chloro-6-(6-(trifluoromethyl)pyridin-2-yl)-N-(2-(trifluoro-methyl)- pyridin- 4-yl)-l ,3,5-triazin-2-amine (201.2 g, 0.48 mmol) in THF (2 L), at room temperature, is added l-amino-2-methylpropan-2-ol (51.3 g, 0.58 mol) and aHC03 (60.5 g, 0.72 mol). The mixture is heated up to reflux for 16 to 24 hrs. The mixture is then concentrated to remove the volatiles and diluted in ethyl acetate, then washed with H20. The organic layer is dried over anhydrous a2S04 and concentrated. The concentrate is then dissolved in dichloromethane and the solvent is removed via rotary evaporator at low temperature (room temperature to 0C). The product is precipitated to afford 2 -methyl- l-(4-(6-(trifluoromethyl)-pyridin-2-yl)-6-(2-(trifluoro- methyl)-pyridin-4-ylamino)-l ,3,5-triazin- 2-ylamino)propan-2-ol, 1H MR (METHANOL-cU) delta 8.62-8.68 (m, 2 H), 8.47-8.50 (m, 1 H), 8.18-8.21 (m, 1 H), 7.96-7.98 (m, 1 H), 7.82-7.84 (m, 1 H), 3.56-3.63 (d, J = 28 Hz, 2 H), 1.30 (s, 6 H); LC-MS: m/z 474.3 (M+H)+.
With sodium hydrogencarbonate; In tetrahydrofuran; at 75 - 80℃; THF (290 mL), 4-chloro-6-(6-(trifluoromethyl)pyridin-2-yl)-N-(2-(trifluoro-methyl)- pyridin-4-yl)-l,3,5-triazin-2-amine (29.0 g, 0.06893 mol), sodium bicarbonate (8.68 g, 0.1033 mol), and 1,1-dimethylaminoethanol (7.37 g, 0.08271 mol) are added to the reaction vessel at 20-35 C. The resulting slurry is heated to reflux (75-80 C) for 16-20 h. The reaction is cooled to 30-40 C and THF evaporated at below 45 C under reduced pressure. The reaction mixture is cooled to 20-35 C and rinsed with ethyl acetate and water, and the ethyl acetate layer collected. The organic layer is concentrated under vacuum at below 45 C then rinsed with dichloromethane and hexanes, filtered and washed with hexanes and dried for 8-1 Oh at 45-50 C under vacuum to provide 2-methyl-l-(4-(6-(trifluoromethyl)pyridin-2-yl)-6-(2-(trifluoromethyl)- pyridin-4-ylamino)-l,3,5-triazin-2-ylamino)propan-2-ol.
With sodium hydrogencarbonate; In tetrahydrofuran; at 75 - 80℃; [00274j THF (290 mL), 4-chloro-6-(6-(trifluoromethyl)pyridin-2-yl)-N-(2-(trifluoro-methyl)- pyridin-4-yl)-i,3,5-triazin-2-amine (29.0 g, 0.06893 mol), sodium bicarbonate (8.68 g, 0.1033 mol), and 1,1-dimethylaminoethanol (7.37 g, 0.0827 1 mol) are added to the reaction vessel at 20-35 C. The resulting slurry is heated to reflux (75-80 C) for 16-20 h. The reaction is cooled to 30-40 C and THF evaporated at below 45 C under reduced pressure. The reaction mixture is cooled to 20-35 C and rinsed with ethyl acetate and water, and the ethyl acetate layer collected. The organic layer is concentrated under vacuum at below 45 C then rinsed with dichloromethane and hexanes, filtered and washed with hexanes and dried for 8-iOh at 45-50 C under vacuum to provide 2-methyl-i -(4-(6-(trifluoromethyl)pyridin-2-yl)-6-(2-(trifluoromethyl)- pyridin-4-ylamino)- 1,3,5 -triazin-2-ylamino)propan-2-ol.
With sodium hydrogencarbonate; In tetrahydrofuran; at 75 - 80℃; THF (290 mL), 4-chloro-6-(6-(trifluoromethyl)pyridin-2-yl)-N-(2-(trifluoro-methyl)- pyridin-4-yl)-l,3,5-triazin-2-amine (29.0 g, 0.06893 mol), sodium bicarbonate (8.68 g, 0.1033 mol), and 1, 1-dimethylaminoethanol (7.37 g, 0.08271 mol) are added to the reaction vessel at 20-35 C. The resulting slurry is heated to reflux (75-80 C) for 16-20 h. The reaction is cooled to 30-40 C and THF evaporated at below 45 C under reduced pressure. The reaction mixture is cooled to 20-35 C and rinsed with ethyl acetate and water, and the ethyl acetate layer collected. The organic layer is concentrated under vacuum at below 45 C then rinsed with dichlorom ethane and hexanes, filtered and washed with hexanes and dried for 8-1 Oh at 45-50 C under vacuum to provide 2-methyl-l-(4-(6-(trifluoromethyl)pyridin-2-yl)-6-(2- (trifluoromethyl)- pyridin-4-ylamino)-l,3,5-triazin-2-ylamino)propan-2-ol.
With sodium hydrogencarbonate; In tetrahydrofuran; at 20 - 80℃; THF (290 mL), 4-chloro-6-(6-(trifluoromethyl)pyridin-2-yl)-N-(2-(trifluoro-methyl)-pyridin-4-yl)-l,3 , 5-triazin-2- amine (29.0 g, 0.06893 mol), sodium bicarbonate (8.68 g, 0.1033 mol), and 1,1-dimethylaminoethanol (7.37 g, 0.08271 mol) were added to the reaction vessel at 20-35C. The resulting slurry was heated to reflux (75-80C) for 16-20 h. The reaction was cooled to 30-40C and THF was evaporated at below 45C under reduced pressure. The reaction mixture was cooled to 20-35C, rinsed with ethyl acetate and water, and the ethyl acetate layer was collected. The organic layer was concentrated under vacuum at below 45C then rinsed with dichloromethane and hexanes, filtered and washed with hexanes and dried for 8-10 h at 45-50C under vacuum to provide 2-methyl-i -(4-(6-(trifluoromethyl)pyridin-2-yl)-6-(2- (trifluoromethyl)-pyridin-4-ylamino)- 1,3,5 -triazin-2-ylamino)propan-2-ol.
With sodium hydrogencarbonate; In tetrahydrofuran; at 20 - 80℃; THF (290 mL), 4-chloro-6-(6-(trifluoromethyl)pyridin-2-yl)-N-(2-(trifluoro-methyl)-pyridin-4-yl)-1,3,5-triazin-2-amine (29.0 g, 0.06893 mol), sodium bicarbonate (8.68 g, 0.1033 mol), and 1,1-dimethylaminoethanol (7.37 g, 0.08271 mol) were added to the reaction vessel at 20-35 C. The resulting slurry was heated to reflux (75-80 C.) for 16-20 h. The reaction was cooled to 30-40 C. and THF was evaporated at below 45 C. under reduced pressure. The reaction mixture was cooled to 20-35 C., rinsed with ethyl acetate and water, and the ethyl acetate layer was collected. The organic layer was concentrated under vacuum at below 45 C. then rinsed with dichloromethane and hexanes, filtered and washed with hexanes and dried for 8-10 h at 45-50 C. under vacuum to provide 2-methyl-1-(4-(6-(trifluoromethyl)pyridin-2-yl)-6-(2-(trifluoromethyl)-pyridin-4-ylamino)-1,3,5-triazin-2-ylamino)propan-2-ol.
With sodium hydrogencarbonate; In tetrahydrofuran; at 20 - 80℃; Example 2, Step 6: Preparation of 2-methyl-1-(4-(6-(trifluoromethyl)pyridin-2-yl)-6-(2-(trifluoromethyl)-pyridin-4-ylamino)-1,3,5-triazin-2-ylamino)propan-2-ol THF (290 mL), 4-chloro-6-(6-(trifluoromethyl)pyridin-2-yl)-N-(2-(trifluoro-methyl)-pyridin-4-yl)-1,3,5-triazin-2-amine (29.0 g, 0.06893 mol), sodium bicarbonate (8.68 g, 0.1033 mol), and 1,1-dimethylaminoethanol (7.37 g, 0.08271 mol) were added to the reaction vessel at 20-35 C. The resulting slurry was heated to reflux (75-80 C.) for 16-20 h. The reaction was cooled to 30-40 C. and THF was evaporated at below 45 C. under reduced pressure. The reaction mixture was cooled to 20-35 C., rinsed with ethyl acetate and water, and the ethyl acetate layer was collected. The organic layer was concentrated under vacuum at below 45 C. then rinsed with dichloromethane and hexanes, filtered and washed with hexanes and dried for 8-10 h at 45-50 C. under vacuum to provide 2-methyl-1-(4-(6-(trifluoromethyl)pyridin-2-yl)-6-(2-(trifluoromethyl)-pyridin-4-ylamino)-1,3,5-triazin-2-ylamino)propan-2-ol.

 

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