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[ CAS No. 79456-34-1 ] {[proInfo.proName]}

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Chemical Structure| 79456-34-1
Chemical Structure| 79456-34-1
Structure of 79456-34-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 79456-34-1 ]

CAS No. :79456-34-1 MDL No. :MFCD10758088
Formula : C6H4BrF3N2 Boiling Point : -
Linear Structure Formula :- InChI Key :QUYZBNHTYCLZLW-UHFFFAOYSA-N
M.W : 241.01 Pubchem ID :20525383
Synonyms :

Calculated chemistry of [ 79456-34-1 ]      Expand+

Physicochemical Properties

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 : 1.0
Molar Refractivity : 41.34
TPSA : 38.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.29 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.64
Log Po/w (XLOGP3) : 2.08
Log Po/w (WLOGP) : 3.61
Log Po/w (MLOGP) : 2.08
Log Po/w (SILICOS-IT) : 2.36
Consensus Log Po/w : 2.35

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.95
Solubility : 0.271 mg/ml ; 0.00113 mol/l
Class : Soluble
Log S (Ali) : -2.53
Solubility : 0.717 mg/ml ; 0.00297 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.41
Solubility : 0.0935 mg/ml ; 0.000388 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.9

Safety of [ 79456-34-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 79456-34-1 ]

* 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.

  • Upstream synthesis route of [ 79456-34-1 ]
  • Downstream synthetic route of [ 79456-34-1 ]

[ 79456-34-1 ] Synthesis Path-Upstream   1~2

  • 1
  • [ 183610-70-0 ]
  • [ 79456-34-1 ]
YieldReaction ConditionsOperation in experiment
98% With N-Bromosuccinimide In acetonitrile at 5 - 23℃; for 1 h; Step 3) 5-Bromo-3-trifluoromethyl-pyridin-2-ylamine CAS-No. [79456-34-11; To a solution of the above 3-trifluoromethyl-pyridin-2-ylamine (16.21 g, 100 mmol) in acetonitrile (300 mL) at 5° C. was added NBS (17.8 g, 100 mmol) and the mixture was stirred at 23° C. for 1 h. Poured into ice and additional sat. NaHCO3-sol., extracted with EtOAc, washed with brine, dried over Na2SO4. Removal of the solvent in vacuum left a yellow solid, which was filtered through a silica gel and cotton wool column with dichloromethane to give the title compound as a yellow solid (23.71 g, 98percent). MS (EI) 240.1 [(M)+], 242.0 [(M+2)+].
93% With N-Bromosuccinimide In acetonitrile at 20℃; Example 46; Preparation of iV-(5-(6-Amino-5-(trifluoromethyl)pyridin-3- yl)thiazolo [5,4-4. Insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The crude product was purified by silica gel column chromatography eluting with a 10percent- 30percent mixture of ethyl acetate and hexane. Concentration of appropriate fractions afforded the titled compound 5-Bromo-3- (trifluoromethyl)pyridin-2-amine (46B, 2.91 g, 93percent) as pale yellow crystalline solid. 1H NMR (300 MHz, CDCl3): δ 8.26 (d, 1 H, J = 1.9 Hz), 7.79 (d, 1 H, J = 1.9 Hz), 5.00 (br s, 2 H). MS (ES) [M+H] calc'd for C6H4BrF3N2 241; found 241.
89.7% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h; Compound BB-21-1 (42.0g, 259mmol) was dissolved in N, N - dimethylformamide (400mL), then was addedN - bromosuccinimide (46.1g, 259mmol).The reaction was stirred at 20 2 hours.The reaction solution was poured into stirred5percent mixture of sodium bisulfite and water (10:1), the precipitate was filtered, washed with water, dissolved in methylene chloride (a 500 mL), dried over sodium sulfatedrying, filtered, and concentrated to give the title compound BB -20-2 (yellow solid, 51.0g, yield: 89.7percent).
88% With N-Bromosuccinimide In N,N-dimethyl-formamide for 4 h; 2-Amino-3-trifluoromethyl pyridine (5.4 gm, 33.3 mmol) was dissolved in DMF (31 mL) and N-bromosuccinimide (5.9 gm, 33.3 mmol) dissolved in DMF (31 mL) was added <n="198"/>dropwise. The mixture was stirred for 4 hours, concentrated to ~ 20 mL and added dropwise into ice-water (600 mL). The product crashed out, was filtered, washed with water (100 mL) and dried under vacuum to afford 5-bromo-3-trifluoromethyl-pyridin-2-ylamine as a light brown solid (7.12 gm, 88percent). 1H NMR (d6-DMSO, 300 MHz) δ 8.22 (s, IH), 7.85 (s, IH), 6.66 (s, 2H); MS (ESI) m/z = 242.9 (MH+).
88% With N-Bromosuccinimide In acetonitrile at 0 - 23℃; for 4 h; N-bromosuccinimide (20.83g, 117.28 mmol) was portion wise added to a stirred solution of 3-(trifluoro- methyl)pyridin-2-amine (19g, 117.28 mmol) in MeCN (380 mL) at 0°C. The RM was stirred for4h at RT. The RM was quenched with aq. NaHCO3 solution (pH—8) and then filtered. The solid was washed with water (200 mL), and the product was dissolved with EtOAc (300 mL). The organic layer was dried over anhydr. Na2SO4, filtered and solvent was concentrated under reduced pressure to give 5-bromo-3-(trifluoromethyl)pyridin-2-amine (25g, 88percent) as a solid.
85% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h; To a solution of 2-amino-3~trifluoromethylpyridine (100 g, 0.62 mol) in D F (500 mL) was added a solution of NBS (1 10 g, 0,62 mol) in DMF (500 mL) dropwise at room temperature. The solution was stirred at room temperature for 2 hours and then concentrated to 300 mL. The residue was added slowly to the beaker containing a mixture of 5percent aqueous NaHS03 and H20 (3 L, 1 :10 v/v). The precipitate was filtered, washed with H20 (2 x 500 mL) and dried under vacuum to give the title compound (120 g, 85percent) as a light brown solid.
84.6% With N-Bromosuccinimide In N,N-dimethyl-formamide at 20℃; for 2 h; Example 1 l-ll-β-Chloro-6-furan-3-yl-8Arifluoromethyl4midazoll,2-a]pyridine-2-carbonyl)-piperidin-4- yl]-pyrrolidin-2-one (Compound 101) Step l 5-Bromo-3-trifluoromethyl-pyridin-2-ylamine[0102] A solution of N-Bromosuccinimide (54.89 g, 308.41 mmol) in DMF (250 niL) was rapidly added dropwise via addition funnel to a stirring solution of 2-Amino-3-(trifluoromethyl) pyridine (50.00 g, 308.41 mmol) in DMF (250 mL) at room temperature. The mixture was stirred for 2 hours, concentrated to a volume of 200 mL and added slowly into a beaker containing a cold stirring mixture of 5percent NaHSO3 and water (1.5 L, 1 :10 v/v). The precipitate was filtered, washed with water (3 x 500 mL) and dried under vacuum to afford 5-bromo-3- trifluoromethyl-pyridin-2-ylamine (62.89 g, 84.6percent) as a light brown solid. MS 242.9 (M+H+).
84.1% With N-Bromosuccinimide In acetonitrile at 0 - 25℃; for 2 h; The 3 - (trifluoromethyl) pyridin-2-amine (1.0g, 6 . 17mmol) dissolved in acetonitrile (30 ml) in, then dropped to 0 °C, then the NBS (1.2g, 6 . 74mmol) is slowly added to the system, is omitted, the temperature is increased to 25 °C reaction 2 hours. The concentrated, the residue by silica gel column chromatography (PE:EA=5:1) purification, to obtain the title compound (1.25g, yield 84.1percent).
82% With bromine In acetic acid at 25 - 30℃; 3-(Trifluoromethyl)-2-pyridinamine (150 g) was added to acetic acid (1500 mL) and stirred the mass for 10 to 15 min. Bromine (47.54 mL) was added to the mixture over a period of 45-60 min at 25-30°C. The reaction mass was maintained under stirring at 25-30°C for 2-3 h. After completion of the reaction, the mass was cooled to 10 to 15°C and diluted with water (2500 mL) subsequently neutralized the mass with solid sodium carbonate (420 g). The reaction mass was filtered and bed was washed with water (300 mL) and dried at 25 to 30°C for 12 h. The dried mass was dissolved in ethyl acetate (2250 mL) and washed with 5percent sodium bicarbonate solution (750 mL). The separated organic layer was washed with 10percent sodium chloride solution (750 mL). Clean organic layer was distilled out completely to obtain the title compound (183 g). Yield: 82percent Purity: 99.52percent 1H NMR (300 MHz, DMSO-<): δ 8.25 (s, 1H), 7.89 (s, 1H), 6.7 (bs, 2H). MS: m/z 242 (M+l)
81% With N-Bromosuccinimide In acetonitrile at 0 - 25℃; for 1 h; To a solution of 3-(trifluoromethyl)pyridin-2-amine (5.4 g, 33.3 mmol) in acetonitrile (100 mL) was added NBS (5.93 g, 33.3 mmol) at OeC and reaction mixture was stirred at 25eC for 1H. After completion of the reaction, reaction mixture was quenched with saturated sodium bicarbonate (25 mL) and extracted with EtOAc (25 mL/13). The combined organic phase was washed with brine (20 mL), dried over Na2S04, filtered. The filtrate was rotary evaporated and residue was purified by flash column chromatography (silica gel) to afford 6.5 g (81percent) of the titled product. 1HNMR (400 MHz, DMSO-d6) U8.28 (d, J = 2.4 Hz, 1H), 7.91 (d, J = 2.4 Hz, 1H), 6.72 (s, 2H); ESI-MS (m/z) 241.08 (MH)\
74% at 20℃; for 2 h; 3-(trifluoromethyl)pyridin-2-amine (20 g, 123 mmol) was stirred in acetic acid (200 ml) at RT. Bromine (19.72 g, 123 mmol) was added drop wise with stirring. The reaction mixture was stirred for 2 h; followed by dilution with water. The product was extracted with ethyl acetate. Organic layer was washed with water, dried over sodium sulfate and concentrated to obtain the title product in 74percent yield.
3.8 g With N-Bromosuccinimide In N,N-dimethyl-formamide for 4 h; Cooling with ice Synthesis of 5-bromo-3-trifluoromethyl-pyridin-2-ylamine
To a stirred solution of R-10 (2.70 g, 16.66 mmol) in DMF (15 ml) is added N-bromosuccinimide (3.00 g, 16.85 mmol) as a DMF solution (15 ml, dropwise).
After 4 h the reaction is poured onto ice.
The resulting precipitate is collected via filtration to give the product as an off-white solid.
Dissolved into DCM and washed with brine.
The layers are separated and the organic phase is dried (MgSO4), filtered and concentrated to give the title intermediate (3.8 g); m/z 241.2/243.2 [M/M+2H].

Reference: [1] Patent: US2007/72879, 2007, A1, . Location in patent: Page/Page column 18
[2] Patent: WO2010/8847, 2010, A2, . Location in patent: Page/Page column 147
[3] Patent: CN105732602, 2016, A, . Location in patent: Paragraph 0364; 0366; 0367; 0368; 0369
[4] Patent: WO2009/23179, 2009, A2, . Location in patent: Page/Page column 196-197
[5] Patent: WO2015/158427, 2015, A1, . Location in patent: Page/Page column 87; 88
[6] Journal of Medicinal Chemistry, 2016, vol. 59, # 3, p. 1078 - 1101
[7] Patent: WO2011/41713, 2011, A2, . Location in patent: Page/Page column 142
[8] Patent: WO2010/91411, 2010, A1, . Location in patent: Page/Page column 79
[9] Patent: CN105541792, 2016, A, . Location in patent: Paragraph 0454; 0455; 0456
[10] Patent: WO2015/145369, 2015, A1, . Location in patent: Page/Page column 36-37
[11] Patent: WO2018/20474, 2018, A1, . Location in patent: Page/Page column 314-315
[12] Patent: WO2012/7926, 2012, A1, . Location in patent: Page/Page column 49
[13] Patent: WO2008/12326, 2008, A1, . Location in patent: Page/Page column 69
[14] Patent: WO2010/139731, 2010, A1, . Location in patent: Page/Page column 135
[15] Patent: WO2012/24150, 2012, A1, . Location in patent: Page/Page column 135
[16] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 16, p. 4652 - 4656
[17] Patent: US2013/195879, 2013, A1, . Location in patent: Paragraph 0278; 0279
[18] ACS Medicinal Chemistry Letters, 2015, vol. 6, # 5, p. 507 - 512
[19] Patent: WO2007/134828, 2007, A1, . Location in patent: Page/Page column 68
[20] Patent: WO2008/138889, 2008, A2, . Location in patent: Page/Page column 85
[21] Patent: WO2008/138834, 2008, A1, . Location in patent: Page/Page column 89
[22] Patent: WO2010/139747, 2010, A1, . Location in patent: Page/Page column 102
  • 2
  • [ 79456-34-1 ]
  • [ 73183-34-3 ]
  • [ 947249-01-6 ]
YieldReaction ConditionsOperation in experiment
97.47% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate In 1,4-dioxane at 25 - 100℃; A mixture of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (180 g) and 1,4-dioxane (3600 mL) was stirred in a flask. Bis(pinacolato)diboron (284.47 g), potassium acetate (109.95 g) and l,l-bis(diphenylphosphino)ferrocene dichloropalladium (II) DCM complex (18 g), were then added under stirring at a temperature of about 25 to 30°C. Reaction mass was heated to 95 to 100°C and maintained for 15-16 hr. After the completion of reaction, the mass was cooled to 25 to 30°C, filtered through celite bed and the bed was washed with ethyl acetate (1800 mL). The filtrate was distilled out completely under vacuum to get crude title compound (450 g). Purification The crude title compound was dissolved in methanol (1800 mL) in a round bottom flask. Charcoal (45 g) and silica gel (60-120 mesh size, 450 g) were added to the mass and maintained under stirring at a temperature of about 25 to 30°C for 1 h. The mass was filtered through celite bed and washed the bed with methanol (450 mL). The filtrate was added into a flask containing cold water (6750 mL) at 0-5°C, over a period of 1 h. The precipitated solid was filtered out, washed with cold water (900 mL). The wet compound was unloaded and dried at 45 to 50°C to obtain the title compound (209 g). Yield: 97.47percent Purity: 98.43percent 1H NMR (300 MHz, DMSO-d6): δ 8.38 (s, 1H), 7.80 (s, 1H), 6.92 (s, 2H), 1.27 (s, 12H). MS: m/z 289.1 (M+l)
94% With potassium acetate In 1,4-dioxane at 110℃; for 10 h; An orange suspension of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (4 g, 16.60 mmol), 4,4,4',4',5,5,5',5'-octamethyl-2,2'-bi(1 ,3,2-dioxaborolane)(5.90 g, 23.24 mmol), KOAc (4.07 g, 41 .5 mmol) and PdCI2(dppf).CH2CI2 (0.678 g, 0.830 mmol) in Dioxane (60 mL) was heated to 1 10°C for 10 h under N2. After concentration under vacuum to remove the solvent, the crude product was purified using a silica gel column, with PE/EtOAc as eluant to give pure product as pale yellow solid (4.5g, yield 94percent). MS (m/z): 289 (M+H)+.
94% With palladium bis[bis(diphenylphosphino)ferrocene] dichloride; potassium acetate In 1,4-dioxane at 110℃; for 10 h; Inert atmosphere An orange suspension of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (4 g, 16.60 mmol), 4,4,4′,4′,5,5,5′,5′-octamethyl-2,2′-bi(1,3,2-dioxaborolane) (5.90 g, 23.24 mmol), KOAc (4.07 g, 41.5 mmol) and PdCl2(dppf).CH2Cl2 (0.678 g, 0.830 mmol) in Dioxane (60 mL) was heated to 110° C. for 10 h under N2. After concentration under vacuum to remove the solvent, the crude product was purified using a silica gel column, with PE/EtOAc as eluant to give pure product as pale yellow solid (4.5 g, yield 94percent). MS (m/z): 289 (M+H)+.
72% With potassium acetate In 1,2-dimethoxyethane at 80℃; Inert atmosphere [0429] To a solution of 5-bromo-3-(trifluoromethyl)pyridin-2-amine (46B, 1.21 g, 5.0 mmol) in DME (50 mL) were added bis(pinacolato)diboron (1.65 g, 6.5 mmol), Pd(dppf)Cl2 CH2Cl2 (122 mg, 0.15 mmol), and potassium acetate (1.47 g, 15 mmol). The mixture was stirred overnight at 80 0C under Ar and then allowed to cool to room temperature. Insoluble materials were removed by filtration and washed with ethyl acetate (100 mL). The filtrate was concentrated in vacuo. The crude product was purified by silica gel column chromatography eluting with a 20percent- 50percent mixture of ethyl acetate and hexane. After concentration of appropriate fractions, the residue was dissolved in ethyl acetate (100 mL), and the solution was washed with saturated aqueous solution of NaHCψ3 (50 mL). The aqueous phase was extracted with ethyl acetate (50 mL). The organic extracts were combined and washed with brine (50 mL) and dried over anhydrous MgSO4. Insoluble materials were removed by filtration and the filtrate was concentrated in vacuo. The residue was re-crystallized from hexane to yield 5-(4,4,5,5-tetramethyl- l,3,2-dioxaborolan-2-yl)-3-(trifluoromethyl)pyridin-2-amine (46C 1.04 g, 72percent) as white crystalline solid. 1H NMR (300 MHz, CDCl3): δ 8.56 (d, 1 H, J = 0.9 Hz), 8.07 (d, 1 H, J = 0.8 Hz), 5.15 (br s, 2 H), 1.33 (s, 12 H). MS (ES) [M+H] calc'd for C6H6BF3N2O2 (In situ hydrolysis of the titled compound to the boronic acid on LC), 207; found 207.

Reference: [1] Patent: WO2015/145369, 2015, A1, . Location in patent: Page/Page column 37
[2] Patent: WO2012/34526, 2012, A1, . Location in patent: Page/Page column 36-37
[3] Patent: US2013/190307, 2013, A1, . Location in patent: Paragraph 0172; 0173
[4] Patent: WO2010/8847, 2010, A2, . Location in patent: Page/Page column 147-148
[5] Patent: WO2008/12326, 2008, A1, . Location in patent: Page/Page column 69
[6] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 16, p. 4652 - 4656
[7] Patent: WO2007/134828, 2007, A1, . Location in patent: Page/Page column 68
[8] Patent: WO2008/138889, 2008, A2, . Location in patent: Page/Page column 85
[9] Patent: WO2008/138834, 2008, A1, . Location in patent: Page/Page column 88-89
[10] Patent: WO2010/139747, 2010, A1, . Location in patent: Page/Page column 102
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