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[ CAS No. 854690-87-2 ] {[proInfo.proName]}

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Chemical Structure| 854690-87-2
Chemical Structure| 854690-87-2
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Quality Control of [ 854690-87-2 ]

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Product Details of [ 854690-87-2 ]

CAS No. :854690-87-2 MDL No. :MFCD09864670
Formula : C7H7BF2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MYJVGNXKXAYCTH-UHFFFAOYSA-N
M.W : 171.94 Pubchem ID :44717244
Synonyms :

Calculated chemistry of [ 854690-87-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.14
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 41.34
TPSA : 40.46 ?2

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) : -6.32 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.45
Log Po/w (WLOGP) : 0.82
Log Po/w (MLOGP) : 1.21
Log Po/w (SILICOS-IT) : 0.13
Consensus Log Po/w : 0.72

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.06
Solubility : 1.51 mg/ml ; 0.00876 mol/l
Class : Soluble
Log S (Ali) : -1.91
Solubility : 2.14 mg/ml ; 0.0124 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.89
Solubility : 2.21 mg/ml ; 0.0129 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 854690-87-2 ]

Signal Word:Danger Class:8,4.1
Precautionary Statements:P210-P240-P241-P260-P264-P270-P273-P280-P301+P312+P330-P301+P330+P331-P303+P361+P353-P304+P340+P310-P305+P351+P338+P310-P363-P370+P378-P405-P501 UN#:2921
Hazard Statements:H228-H302-H314-H412 Packing Group:Ⅱ
GHS Pictogram:

Application In Synthesis of [ 854690-87-2 ]

* 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 [ 854690-87-2 ]

[ 854690-87-2 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 787575-92-2 ]
  • [ 854690-87-2 ]
  • [ 854690-78-1 ]
YieldReaction ConditionsOperation in experiment
71% With potassium phosphate;(1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; In methanol; 1,2-dimethoxyethane; at 82℃; PREPARATION 90 7- (3-difluoromethylphenyl)-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide Dissolve [2- (7-bromo-isoquinoline-5-sulfonylamino)-ethyl]-carbamic acid tert- butyl ester (0.13 g, 0.30 mmol) and 3- (difluoromethyl) phenylboronic acid (0.057 g, 0.33 mmol) in DME-methanol (8: 1,10 ml). To the mixture, add K3P04 (0.13 g, 0.60 mmol), and PdCl2 (dppf) (0.012 g, 0.015 mmol). Heat this mixture at 82 °C overnight. Cool the reaction mixture, dilute with water and extract with EtOAc. Wash with brine and evaporate to dryness. Purify by silica gel chromatography to give the desired compound (0.10 g, 71percent yield) :'H NMR (CDC13): J9. 39 (s, 1H), 8.66 (m, 2H), 8.43 (d, J= 5.7 Hz, 2H), 7.86 (m, 2H), 7.61 (m, 2H), 6. 76 (t, J= 52.1 Hz, 1H), 5.00 (br s, 1H), 3. 18 (m, 2H), 3.03 (m, 2H), 1.37 (s, 9H); ESIMS : m/z 478 (M+H) +.
  • 2
  • [ 854690-87-2 ]
  • [ 1569649-68-8 ]
  • [ 1569649-74-6 ]
YieldReaction ConditionsOperation in experiment
55% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In water; acetonitrile; at 75℃; for 2h; General procedure: Preparation 4 5-(3-Difluoromethyl-phenyl)-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid A mixture of 5-bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 3c, 3.00 g, 8.32 mmol, based on 76percent purity), 3-(difluoromethyl)-phenylboronic acid (2.30 g, 13 mmol), 1,1'-[bis(diphenylphosphino)ferrocene]-dichloropalladium(II) (690 mg, 0.94 mmol) and 2 M aqueous K2CO3 solution (10 mL, 20 mmol) in acetonitrile (20 mL) is heated for 2 h at 75° C. The reaction mixture is diluted with methanol and purified by preparative reversed phase HPLC (XBridge, gradient of acetonitrile in water, 0.3percent NH4OH, 30° C.). Yield: 1.46 g (55percent of theory); ESI mass spectrum: [M+H]+=322; Retention time HPLC: 0.92 min (Z018_S04).
1.46 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In water; acetonitrile; at 75℃; for 2h; A mixture of 5-bromo-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid (preparation 3c, 3.00 g, 8.32 mmol, based on 76percent purity), 3-(difluoromethyl)- phenylboronic acid (2.30 g, 13 mmol), 1,1 '-[bis(diphenylphosphino)ferrocene]- dichloropalladium(II) (690 mg, 0.94 mmol) and 2 M aqueous K2CO3 solution (10 mL, 20 mmol) in acetonitrile (20 mL) is heated for 2 h at 75°C. The reaction mixture is diluted with methanol and purified by preparative reversed phase HPLC (XBridge, gradient of acetonitrile in water, 0.3percent NH4OH, 30°C). Yield: 1.46 g (55 percent of theory); ESI mass spectrum: [M+H]+ = 322; Retention time HPLC: 0.92 min (Z018 S04).
  • 3
  • [ 854690-87-2 ]
  • [ 1570077-28-9 ]
  • [ 1570075-93-2 ]
YieldReaction ConditionsOperation in experiment
42% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In water; acetonitrile; at 75℃; for 18h; General procedure: Example 1 5-(3-Difluoromethyl-phenyl)-1-isopropyl-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-(N-cyano-S-methylsulfonimidoyl)-benzylamide To a solution of preparation 1 (70 mg, 0.15 mmol), <strong>[854690-87-2]3-(difluoromethyl)phenylboronic acid</strong> (36 mg, 0.21 mmol) and 1,1'-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (11 mg, 0.015 mmol) in acetonitrile (2.00 mL) is added aqueous K2CO3 solution (2 M, 0.155 mL, 0.31 mmol). After stirring for 18 h at 75° C., the reaction mixture is filtered and the filtrate is purified by preparative reversed phase HPLC(XBridge, gradient of methanol in water, 0.1percent NH4OH, 60° C.). Yield: 32 mg (42percent of theory); ESI mass spectrum: [M+H]+=513; r.t. HPLC: 0.90 min (Z003-001).
42% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium carbonate; In water; acetonitrile; at 75℃; for 18h; To a solution of preparation 1 (70 mg, 0.15 mmol), <strong>[854690-87-2]3-(difluoromethyl)phenylboronic acid</strong>(36 mg, 0.21 mmol) and 1, 1'-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (11mg, 0.015 mmol) in acetonitrile (2.00 mL) is added aqueous K2C03 solution (2M, 0.155mL, 0.31 mmol). After stirring for 18 hat 75°C, the reaction mixture is filtered and the filtrate is purified by preparative reversed phase HPLC (XBridge, gradient of methanol inwater, 0.1percent NH40H, 60°C). Yield: 32 mg (42percent oftheory); ESI mass spectrum: [M+Ht= 513; r.t. HPLC: 0.90 min (Z003_001).
  • 4
  • [ 854690-87-2 ]
  • [ 1571135-36-8 ]
  • [ 1571134-60-5 ]
YieldReaction ConditionsOperation in experiment
90 mg With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; acetonitrile; at 75℃; for 18h; To a solution of 5-bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide (preparation 11, 110 mg, 0.208 mmol), 3-difluoromethyl-phenylboronic acid (48 mg, 0.28 mmol), palladium (0) tetrakis(triphenylphosphine) (32 mg, 0.028 mmol) in acetonitrile (2 mL) is added 2 M aqueous K2CO3 solution (0.21 mL, 0.42 mmol). After stirring for 18 h at 75° C., the reaction mixture is diluted with methanol, acidified with acetic acid and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.1percent TFA, 60° C.). Yield: 90 mg (75percent of theory); ESI mass spectrum: [M+H]+=576; Retention time HPLC: 1.03 min (Z018_S04).
90 mg With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; acetonitrile; at 75℃; for 18h; To a solution of 5-bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-l,4-dihydro- pyridine-3-carboxylic acid 4-methanesulfonyl-benzylamide (preparation 11, 110 mg, 0.208 mmol), 3-difluoromethyl-phenylboronic acid (48 mg, 0.28 mmol), palladium (0) tetrakis(triphenylphosphine) (32 mg, 0.028 mmol) in acetonitrile (2 mL) is added 2 M aqueous K2CO3 solution (0.21 mL, 0.42 mmol). After stirring for 18h at 75°C, the reaction mixture is diluted with methanol, acidified with acetic acid and purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.1percent TFA, 60°C). Yield: 90 mg (75percent of theory); ESI mass spectrum: [M+H]+ = 576; Retention time HPLC: 1.03 min (Z018_S04).
  • 5
  • [ 854690-87-2 ]
  • [ 1571135-36-8 ]
  • [ 1571134-62-7 ]
  • [ 1571134-61-6 ]
  • 6
  • [ 854690-87-2 ]
  • [ 1571135-34-6 ]
  • [ 1571133-56-6 ]
YieldReaction ConditionsOperation in experiment
71% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; acetonitrile; at 75℃; for 18h; To a solution of 5-bromo-l-[l-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-l,4-dihydro- pyridine-3-carboxylic acid methylamide (preparation 9, 100 mg, 0.267 mmol), 3- difluoromethyl-phenylboronic acid (67 mg, 0.390 mmol), palladium (0) tetrakis(triphenylphosphine) (25 mg, 0.022 mmol) in acetonitrile (2 mL) is added 2 M aqueous K2CO3 solution (0.30 mL, 0.60 mmol). After stirring for 18h at 75°C, the reaction mixture is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.1percent NH4OH, 60°C). Yield: 80 mg (71percent of theory); ESI mass spectrum: [M+H]+ = 422; Retention time HPLC: 0.99 min (Z018 S04)
80 mg With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In water; acetonitrile; at 75℃; for 18h; To a solution of 5-bromo-1-[1-(4-cyano-phenyl)-ethyl]-6-methyl-4-oxo-1,4-dihydro-pyridine-3-carboxylic acid methylamide (preparation 9, 100 mg, 0.267 mmol), 3-difluoromethyl-phenylboronic acid (67 mg, 0.390 mmol), palladium (0) tetrakis(triphenylphosphine) (25 mg, 0.022 mmol) in acetonitrile (2 mL) is added 2 M aqueous K2CO3 solution (0.30 mL, 0.60 mmol). After stirring for 18 h at 75° C., the reaction mixture is purified by preparative reversed-phase HPLC (XBridge, gradient of methanol in water, 0.1percent NH4OH, 60° C.). Yield: 80 mg (71percent of theory); ESI mass spectrum: [M+H]+=422; Retention time HPLC: 0.99 min (Z018_S04).
  • 7
  • [ 854690-87-2 ]
  • 5-(4-chlorophenyl)-2-({5-[(1RS)-1-hydroxyethyl]-1H-1,2,4-triazol-3-yl}methyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one [ No CAS ]
  • 5-(4-chlorophenyl)-2-({1-[3-(difluoromethyl)phenyl]-5-[(1RS)-1-hydroxyethyl]-1H-1,2,4-triazol-3-yl}methyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
47 mg With pyridine; copper diacetate; at 20℃; for 120h; Example 19 5-(4-Chlorophenyl)-2-({1-[3-(difluoromethyl)phenyl]-5-[(1RS)-1-hydroxyethyl]-1H-1,2,4-triazol-3-yl}methyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (diastereomeric mixture) To a solution of 5-(4-chlorophenyl)-2-({5-[(1RS)-1-hydroxyethyl]-1H-1,2,4-triazol-3-yl}methyl)-4-[(2S)-3,3,3-trifluoro-2-hydroxypropyl]-2,4-dihydro-3H-1,2,4-triazol-3-one (400 mg, 0.74 mmol, 80percent purity) in pyridine (9.6 ml) were added <strong>[854690-87-2][3-(difluoromethyl)phenyl]boronic acid</strong> (254.26 mg, 1.48 mmol) and copper(II) acetate (268.6 mg, 1.48 mmol). The reaction mixture was heated to 60° C. for 2 h and then stirred at room temperature for 5 days. The resulting reaction mixture was concentrated in vacuo, then diluted with ethyl acetate and quenched with aqueous hydrochloric acid (0.5 M). After phase separation, the aqueous phase was extracted twice with ethyl acetate. The combined organic phases were dried over sodium sulfate, filtered, and concentrated in vacuo. The crude product was purified by preparative HPLC [method 4], and the desired compound (47 mg, 0.08 mmol) was obtained as a mixture of diastereomers (yield 11.3percent). LC/MS [method 1]: Rt=1.04 min; MS [ESIpos]: m/z=559 (M+H)+ 1H NMR (400 MHz, DMSO-d6): delta [ppm] 1.47 (d, 3H), 3.85 (dd, 1H), 4.01 (dd, 1H), 4.24-4.36 (m, 1H), 4.81 (q, 1H), 5.02-5.13 (m, 2H), 5.74 (br. s, 1H), 6.89 (br. s, 1H), 7.14 (t, 1H), 7.59-7.65 (m, 2H), 7.69-7.78 (m, 4H), 7.81-7.87 (m, 2H).
  • 8
  • [ 854690-87-2 ]
  • (4S)-7-chloro-8-methyl-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine [ No CAS ]
  • (4S)-7-(3-(difluoromethyl)phenyl)-8-methyl-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
50.8% A suspension of (4S)-7-chloro-8-methyl-2,3,4,5-tetrahydro-l,4-methanopyrido[2,3- b][l,4]diazepine (400 mg, 1.908 mmol),<strong>[854690-87-2](3-(difluoromethyl)phenyl)boronic acid</strong> (328 mg, 1.908 mmol) and potassium carbonate (791 mg, 5.72 mmol) in 1,4-Dioxane (15 mL) & Water (4 mL) stirred and degassed with argon at room temp for 15 min, PdCl2(dppf)- CH2C12 adduct (1558 mg, 1.908 mmol) was added to the reaction mixture. Then the reaction mixture was stirred 16 hr at 90 C. The reaction mixture was cooled to room temp, and filtered through celite and washed with EtOAc (100 ml). Filtrate was concentrated and dissolved with EtOAc (50 ml).EtOAc layer washed with water (50 ml) followed by brine solution (50 ml) and dried out with Na2S04, filtered and concentrated to get crude product. The crude product was purified by column chromatography using silica gel(100-200) and was eluted with 50% EtOAc in Hexane (gradient system) to afford the desired product (4S)-7-(3-(difluoromethyl)phenyl)-8-methyl-2,3,4,5-tetrahydro-l,4- methanopyrido[2,3-b][l,4]diazepine (300 mg, 0.969 mmol, 50.8 % yield) as a pale yellow solid LCMS (w/z):302.1 1 [M+H]+.
  • 9
  • [ 854690-87-2 ]
  • (4S)-7,8-dichloro-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine [ No CAS ]
  • (4S)-8-chloro-7-(3-(difluoromethyl)phenyl)-2,3,4,5-tetrahydro-1,4-methanopyrido[2,3-b][1,4]diazepine [ No CAS ]
YieldReaction ConditionsOperation in experiment
A suspension of (4S)-7,8-dichloro-2,3,4,5-tetrahydro-l,4-methanopyrido[2,3- b][l,4]diazepine (400 mg, 1.738 mmol),<strong>[854690-87-2](3-(difluoromethyl)phenyl)boronic acid</strong> (299 mg, 1.738 mmol) and potassium carbonate (721 mg, 5.22 mmol) in 1,4-Dioxane (10 mL) & Water (1.5 mL) stirred and degassed with argon at room temp for 15 mins, PdCl2(dppf)- CH2C12 adduct (1420 mg, 1.738 mmol) was added to the reaction mixture. Then the reaction mixture was stirred 16 hr at 90 C. The reaction mixture was cooled to room temp, and filtered through celite and washed with EtOAc (100 ml). Take filtrate and concentrated and dissolved with EtOAc (50 ml).EtOAc layer washed with water (100 ml) followed by brine solution (100 ml) and dried out with Na2S04, filtered and concentrated to get crude product. The crude product was purified by column chromatography using silica gel(l 00-200) and was eluted with 50% EtOAc in Hexane (gradient system) to afford the desired product (4S)-8-chloro-7-(3-(difluoromethyl)phenyl)-2,3,4,5-tetrahydro-l,4- methanopyrido[2,3-b][l,4]diazepine (500 mg, 1.554 mmol, 89 % yield) as a pale yellow solid, LCMS (m/z): 302.1 1 [M+H]+.
  • 10
  • [ 854690-87-2 ]
  • N-(5-(3-(difluoromethyl)benzyl)pyridin-2-yl)-1-methyl-6-oxo-1,4,5,6-tetrahydropyridazine-3-carboxamide [ No CAS ]
  • 11
  • [ 854690-87-2 ]
  • 5-(3-(difluoromethyl)benzyl)pyridin-2-amine [ No CAS ]
  • 12
  • [ 854690-87-2 ]
  • [ 70258-18-3 ]
  • 2-chloro-5-(3-(difluoromethyl)benzyl)pyridine [ No CAS ]
YieldReaction ConditionsOperation in experiment
58% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium carbonate; In water; acetonitrile; at 50℃; for 1h;Inert atmosphere; To a solution of <strong>[854690-87-2](3-(difluoromethyl)phenyl)boronic acid</strong> (0.405 g, 2.5 mmol) and 2-chloro-5-(chloromethyl)pyridine (0.430 g, 2.5 mmol) and potassium carbonate (0.691 g, 5 mmol) in acetonitrile (70 ml_) and water (10 ml_) was added [1 ,1 '-b/s(diphenylphosphino)ferrocene]dichloropalladium(ll) dichloromethane (0.204 g, 0.25 mmol) under argon. The mixture was stirred at 50 C for 1 h. Volatiles were removed under reduced pressure and water (50 ml_) was added. The aqueous layer was extracted with ethyl acetate (80 ml_ x 3), dried with sodium sulfate, filtered and concentrated. The crude material was purified by column chromatography (silica gel, petroleum ether/ethyl acetate = 12/1 ) to give 2-chloro-5-(3-(difluoromethyl)benzyl)pyridine (0.397 g, 1 .45 mmol, 58%) as a colorless oil. LCMS (ESI) m/z: 254.1 [M+H]+.
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; ;