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CAS No. : | 887707-25-7 | MDL No. : | MFCD12024302 |
Formula : | C6H2ClF3IN | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KUASPTUGCBGXAE-UHFFFAOYSA-N |
M.W : | 307.44 | Pubchem ID : | 11500513 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.17 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 46.97 |
TPSA : | 12.89 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -5.8 cm/s |
Log Po/w (iLOGP) : | 2.11 |
Log Po/w (XLOGP3) : | 3.35 |
Log Po/w (WLOGP) : | 4.51 |
Log Po/w (MLOGP) : | 3.05 |
Log Po/w (SILICOS-IT) : | 4.01 |
Consensus Log Po/w : | 3.41 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.16 |
Solubility : | 0.0212 mg/ml ; 0.0000691 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -3.3 |
Solubility : | 0.155 mg/ml ; 0.000503 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -4.46 |
Solubility : | 0.0106 mg/ml ; 0.0000344 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 2.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 2.16 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302+H312+H332-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | at 100℃; | Step B. 2-chloro-5-iodo-3-(trifluoromethyl)Dyridine A suspension of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (3.0 g, 10.4 mmol) in POCI3 (8 mL) was heated at 100 °C overnight. After cooling down to room temperature, the mixture was poured into ice (50 g). The resulting aqueous layer was neutralized by Na2C03 and extracted with ethyl acetate (70 mL x 2). The extracts were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether:EtOAc (100: 1-4: 1) as eluting solvents to afford 2- chloro-5-iodo-3-(trifluoromethyl)pyridine as a white solid (2.0 g, 63percent). 1H NMR (500 MHz, CDCls) δ (ppm) 8.78 (d, J = 2.0 Hz, 1H), 8.28 (d, J = 2.0 Hz, 1H). |
63% | at 100℃; | Step B. 2-chloro-5-iodo-3-(trifluoromethyl)pyridine A suspension of 5-iodo-3-(trifluoromethyl)pyridin-2-ol (3.0 g, 10.4 mmol) in POCI3 (8 mL) was heated at 100 °C overnight. After cooling down to room temperature, the mixture was poured into ice (50 g). The resulting aqueous layer was neutralized by Na2C03 and extracted with EtOAc (70 mL x 2). The extracts were combined, dried over sodium sulfate, filtered, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using petroleum ether:EtOAc (100: 1-4: 1) as eluting solvents to afford 2- chloro-5-iodo-3-(trifluoromethyl)pyridine as a white solid (2.0 g, 63percent). 1H NMR (500 MHz, CDC13) δ (ppm) 8.78 (d, / = 2.0 Hz, 1H), 8.28 (d, / = 2.0 Hz, 1H). |
62% | With trichlorophosphate In N,N-dimethyl-formamide at 110℃; for 0.333333 h; Microwave irradiation | 2-choro-5-iodo-3-trifluoromethylpyridine[0072] To an ice-cold mixture OfPOCl3 (1.60 mL) and DMF (1 mL) in a microwave vial, 5-iodo-3-trifluoromethyl-2-pyridinol (1 g, 3.47 mmol) is added. The vial is sealed and heated 20 min at 110 0C. The reaction mixture cooled at room temperature is poured into ice cold water. The product precipitates. The precipitate is filtered, washed with cold water and dried to afford 661 mg (62 percent) of a light brown powder. <n="51"/>[0073] 1U NMR (500 MHz CDCl3) δ 8.32 (d, J=2.0 Hz, IH), 8.81 (d, J=2.0 Hz,IH). 13C NMR (250 MHz CDCl3) δ 89.4, 121.2 (q, JC-F= 273.3 Hz), 126.8 (q, JC-F= 33.6 Hz), 144.34, 148.5, 158.7. |
55% | With trichlorophosphate In N,N-dimethyl-formamide at 130℃; for 0.333333 h; Microwave irradiation | Then in DMF, 2-hydroxy-3-trifluoromethyl-5- (iodo) pyridine I wasmixed with POCl3, and was heated for 20 minutes in a microwave at130 ° C, and 2-chloro-3-trifluoromethyl -5 - (iodo) pyridine J (yield of 50percent to55percent) is formed. |
55% | With trichlorophosphate In N,N-dimethyl-formamide at 130℃; for 0.333333 h; Microwave irradiation | A solution of 2-hydroxy-3-(trifluoromethyl)pyridine C in a mixture of N-iodosuccinimide (NIS), acetonitrile, and dimethylformamide (DMF) is heated at 80° C. for 2 hours to produce 2-hydroxy-3-trifluoromethyl-5-(iodo)pyridine I (greater than 80percent yield). The 2-hydroxy-3-trifluoromethyl-5-(iodo)pyridine I is then mixed with POCl3 in DMF and heated to 130° C. in a microwave for 20 minutes to produce 2-chloro-3-trifluoromethyl-5-(iodo)pyridine J (yield of 50 to 55percent). The 2-chloro-3-trifluoromethyl-5-(iodo)pyridine K is reacted in a solution of pMBnNH2, palladium(II) acetate, 2,2′-bis(diphenylphosphino)-1,1′-binaphthyl (BINAP), triethylamine, and cesium carbonate in toluene to produce 5-((4-methoxyphenyl))methylamino)-2-chloro-3-(trifluoromethyl)pyridine K (yield of 40percent). The 5-((4-methoxyphenyl))methylamino)-2-chloro-3-(trifluoromethyl)pyridine K is reacted in a solution of zinc cyanide, tris(dibenzylideneacetone)dipalladium (Pd2(dba)3), and 1,1′-bis(diphenylphosphino)ferrocene (dppf) in DMF to provide 5-(4-methoxybenzylamine)-2-cyano-3-(trifluoromethyl)pyridine K (yield of 92percent). The 5-(4-methoxybenzylamine)-2-cyano-3-(trifluoromethyl)pyridine K is reacted in a solution of dichloromethane and trifluoroacetic acid to provide 2-cyano-3-trifluoromethyl-5-(amino)pyridine H (yield greater than 95percent). The 2-cyano-3-trifluoromethyl-5-(amino)pyridine H is reacted with thiophosgene in water at 25° C. for 2 hours to provide 5-isothiocyanato-3-(trifluoromethyl)pyridine-2-carbonitrile A (yield of 74percent to 95percent). |
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