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[ CAS No. 1166829-70-4 ] {[proInfo.proName]}

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Chemical Structure| 1166829-70-4
Chemical Structure| 1166829-70-4
Structure of 1166829-70-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1166829-70-4 ]

CAS No. :1166829-70-4 MDL No. :MFCD18383324
Formula : C16H27BO4 Boiling Point : -
Linear Structure Formula :- InChI Key :QIAHVZXOVXLJRI-UHFFFAOYSA-N
M.W :294.19 Pubchem ID :57992079
Synonyms :

Calculated chemistry of [ 1166829-70-4 ]

Physicochemical Properties

Num. heavy atoms : 21
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.81
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 84.67
TPSA : 44.76 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.03 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.91
Log Po/w (WLOGP) : 3.3
Log Po/w (MLOGP) : 1.96
Log Po/w (SILICOS-IT) : 2.21
Consensus Log Po/w : 2.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.17
Solubility : 0.2 mg/ml ; 0.00068 mol/l
Class : Soluble
Log S (Ali) : -3.51
Solubility : 0.0907 mg/ml ; 0.000308 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.54
Solubility : 0.0839 mg/ml ; 0.000285 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.35

Safety of [ 1166829-70-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1166829-70-4 ]

* 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 [ 1166829-70-4 ]

[ 1166829-70-4 ] Synthesis Path-Downstream   1~81

  • 1
  • [ 1166829-70-4 ]
  • [ 121219-03-2 ]
  • [ 1166829-68-0 ]
YieldReaction ConditionsOperation in experiment
43.5% With potassium carbonate;1,1 bis(di-tert-butylphosphino)ferrocene palladium dichloride; In N,N-dimethyl-formamide; at 20 - 100℃; for 4h; Intermediate 43-6: Ethyl 2-f4-f2-fluoro-4-hvdroxyphenyl)cvclohex-3-enyl)acetateA solution of Intermediate 43-7 (18.48 g, 62.82 mmol) in DMF (100 mL) was added to a stirred suspension of <strong>[121219-03-2]4-bromo-3-fluorophenol</strong> (10 g, 52.36 mmol), potassium carbonate (21.71 g, 157.07 mmol) and [l,l-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.163 g, 1.41 mmol) in DMF (100 mL) at ambient temperature. The resulting suspension was stirred at 80 0C under nitrogen for 2 hours. The reaction was incomplete so the temperature was increased to 100 0C and the reaction mixture was stirred for a further 30 minutes and then further [l,l-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (1.163 g, 1.41 mmol) was added and the suspension was stirred at 100 0C for a further 45 minutes and then further [l,l-Bis(diphenylphosphino)ferrocene]dichloropalladium(II) (400 mg, 0.487 mmol) was added and the suspension was stirred at 100 0C for a further 45 minutes. The reaction mixture was evaporated to dryness and redissolved in EtOAc (200 mL) and 2M HCl (250 mL) was cautiously added. The aqueous layer was further extracted with EtOAc (3 x 200 mL) and the organic extracts were combined, washed saturated brine (300 mL), dried over MgSO4, filtered and evaporated to afford crude product. The crude <n="133"/>product was purified by flash silica chromatography, elution gradient 0 to 20% EtOAc in isohexane. Pure fractions were evaporated to dryness to afford the title compound (6.34 g, 43.5 %) as a pale yellow oil.1H NMR (400 MHz, CDCl3) delta 1.27 (3H, t), 1.41 - 1.50 (IH, m), 1.85 - 1.95 (2H, m), 2.14 - 2.21 (IH, m), 2.32 (2H, d), 2.32 - 2.48 (3H, m), 4.16 (2H, q), 4.98 (IH, s), 5.81 (IH, s), 6.51 - 6.56 (2H, m), 7.05 - 7.09 (IH, m); m/z 277 (M-H)".
  • 3
  • [ 1166829-72-6 ]
  • [ 73183-34-3 ]
  • [ 1166829-70-4 ]
YieldReaction ConditionsOperation in experiment
73.5% Step 2. Ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l- yl)acetate. A vial was charged with ethyl 2-[4-(trifluoromethanesulfonyloxy)cyclohex-3-en-l- yl] acetate (1.71 g, 0.01 mol), l,l'-bis(diphenylphosphino)ferrocene (150 mg, 0.27 mmol), potassium acetate (1.59 g, 16.2 mmol) and bis(pinacolato)diboron (1.51 g, 5.94 mmol). The vial was purged with N2 (x3), then dioxane (5.4 mL) was added and the mixture degassed for 5 min. [l,r-Bis(diphenylphosphino)ferrocene]dichloropalladium(II)complex with dichloromethane (221 mg, 0.27 mol) was then added and the resulting mixture degassed again for 5 min. The resulting orange reaction mixture was stirred at 80C overnight. After 18 h, the reaction was cooled to room temperature. A saturated aqueous solution of NaHCCb (2 mL) was added and the aqueous layer was extracted with EtOAc (3 x 2 mL). The organic layers were combined and removed solvent in vacuo. Purified by flash chromatography (silica, 0- 10% MeOH/DCM) to afford the title compound (1.17 g, 73.5%). 1H NMR (400 MHz, CDCb) d 6.52 (d, / = 1.96 Hz, 1H), 4.14 (d, / = 7.09 Hz, 2H), 1.99 - 2.36 (m, 6H), 1.69 - 1.91 (m, 2H), 1.55 (s, 1H), 1.21 - 1.34 (m, 15H).
51% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃;Inert atmosphere; ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl)acetate 1b (3.0 g, 9.3 mmol), bis(pinacolato)diboron (2.9g, 11.4mmol), Potassium acetate (1.86 g, 19.0 mmol),[1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (347 mg, 0.47 mmol) and 1,4-dioxane (40 ml) were heated to 80 C under nitrogen and stirred for overnight. Cooled to room temperature, the solvent was removed under reduced pressure and the residue was purified by silica gel column chromatography (0-10% ethyl acetate / petroleum ether) used, To give the desired product ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)acetate 35a (1.4 g, white solid), yield: 51%.
50.2% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 80℃; for 16h;Inert atmosphere; In 2 liter 4 neck flask was taken ethyl 2-(4-(((trifluoromethyl)sulfonyl)oxy)cyclohex-3-en-1-yl)acetate (120 g, 379 mmol), BISPN (106 g, 417 mmol), and potassium acetate (112 g, 1138 mmol) in 1,4-dioxane (1200 mL) under nitrogen. Nitrogen was purged inside the reaction mixture for 10 minutes. Then 1,1 ‘-bis(diphenylphosphino) ferrocene-palladium dichloride dichloromethane complex (15.49 g, 18.97 mmol) was added. The reaction mixture was heated at 80 C for 16 h. The reaction mixture wasconcentrated. The residue was partitioned between ethyl acetate and water, filtered through CELITE bed. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3X). Combined organic layer was washed with water, brine, and dried over sodium sulfate and concentrated in vacuo. The crude material was purified through flash column chromatography, eluting with 0-10% ethyl acetate in petroleumether to give Intermediate 164E (pale yellow oil, 56 g, 190 mmol, 50.2% yield). GC-MS Anal. Calc’d for C,6H27B04, 294.20 found [M] 295.3. T = 1.10 mm (Method A). ‘H NMR (400MHz, chloroform-d) ö: 6.52 (dd, J=4.i, 1.9 Hz, 1H), 4.14 (q, J=7.i Hz, 2H), 2.62- 1.97 (m, 6H), 1.94- 1.68 (m, 2H), 1.33- 1.21 (m, 16H).
50.2% With dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; potassium acetate; In 1,4-dioxane; at 80℃; for 16h;Inert atmosphere; In 2 liter 4 neck flask was taken Intermediate 154D (120 g, 379 mmol), bis(pinacolato)diboron (106 g, 417 mmol), and potassium acetate (112 g, 1138 mmol) in 1,4-dioxane (1200 mL) under nitrogen. Nitrogen was purged inside the reaction mixture for 10 minutes. Then 1 , 1 '-bis(diphenylphosphino)ferrocene -palladium dichloride dichloromethane complex (15.49 g, 18.97 mmol) was added. The reaction mixture was heated at 80 C for 16 h. The reaction mixture was concentrated. The residue was partitioned between ethyl acetate and water, filtered through CELITE bed. The organic layer was separated and the aqueous layer was extracted with ethyl acetate (3X). Combined organic layer was washed with water, brine, and dried over sodium sulfate and concentrated in vacuo. The crude material was purified through flash column chromatography, eluting with 0-10% ethyl acetate in petroleum ether to give Intermediate 154E (pale yellow oil, 56 g, 190 mmol, 50.2% yield). GC-MS Anal. Calc'd for Ci6H27B04, 294.20 found [M+H]+ 295.3. Tr = 1.10 min (Method A). 1H NMR (400MHz, chloroform-d) δ: 6.52 (dd, J=4.1, 1.9 Hz, 1H), 4.14 (q, J=7.1 Hz, 2H), 2.62 - 1.97 (m, 6H), 1.94 - 1.68 (m, 2H), 1.33 - 1.21 (m, 16H)
With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; potassium acetate; In 1,4-dioxane; at 95℃; for 18h;Inert atmosphere; To a mixture of ethyl 2- (4- ( ( (trifluoromethyl) sulfonyl) oxy) cyclohex-3-en-1-yl) acetate (30.32 g, crude, 96 mmol, 1.00 eq) dissolved in 1, 4-dioxane (400 ml) , 4, 4, 4', 4', 5, 5, 5', 5'-octamethyl-2, 2'-bi (1, 3, 2-dioxaborolane) (26.8 g, 106 mmol, 1.10 eq) , CH 3COOK (38.02 g, 192 mmol, 2.00 eq) and Pd (dppf) Cl 2 (14.04 g, 19.2 mmol, 0.20 eq) were added. The mixture was stirred at 95 under nitrogen protection for 18 hours. The solution was filtered and concentrated to dryness. The crude (12.50 g, 100 %yield) was filtered through the silica gel pad and washed with PE/EA = 6: 1. The filtrate was concentrated to dryness to give a black oil (33.2 g, 112.3 %yield) which was used in next step without further purification. 1H NMR (CDCl 3) δ H 6.51 (s, 1H) , 4.13 (q, J = 7.2 Hz, 3H) , 1.99-2.40 (m, 9H) , 1.68-1.94 (m, 3H) and 1.18-1.26 (m, 12H) .

  • 4
  • [ 1166829-70-4 ]
  • [ 13631-21-5 ]
  • [ 1166829-95-3 ]
  • 5
  • [ 1166829-70-4 ]
  • [ 19524-06-2 ]
  • C15H19NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 85℃; for 24h; Prepared using General Procedures Q, P, G, H, K, L, M. In General Procedure Q, 4-bromopyridine hydrochloride was used. In General Procedure P, AcOH and Degussa Pd/C were used. In General Procedure H, 3-chloroaniline was used. In General Procedure L, NaHC03 was replaced with K2C03. The desired products were obtained as a mixture of diastereomers as an off-white solid. 1H NMR (400 MHz, CD3OD): δ 8.40- 8.33 (m, 2H), 7.33-7.23 (m, 3H), 7.17 - 7.08 (m, 2H), 7.14-7.04 (m, 1H), 2.56-2.42 (m, 2H), 2.32 (d, J= 7.2 Hz, 1H), 1.81 (t, J= 13.0 Hz, 3H), 1.63 - 1.16 (m, 5H), 1.15 - 0.98 (m, 1H) ppm. m/z 172.7 (M+2H)2+.
  • 8
  • [ 391-77-5 ]
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6-fluoroquinolin-4-yl)cyclohex-3-en-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
95% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Sealed tube; Inert atmosphere; Ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l- yl)acetate (Intermediate 154E) (5 g, 17.00 mmol) was taken up in dioxane (28.3 ml) and water (7.08 ml). 4-Chloro-6-fluoroquinoline (2.57 g, 14.15 mmol) was added followed by K2C03 (5.87 g, 42.5 mmol). Mixture was bubble with nitrogen gas for 5 minutes before the addition of Pd(Ph3P)4 (0.327 g, 0.283 mmol). After addition, reaction was vacated and backfilled with N2 three times and then sealed (sealed vial parafilmed) and heated to 100 C for 16 hours. The reaction was concentrated in vacuo and purified directly via silica gel flash column chromatography to give Intermediate 154F (4.22 g, 13.47 mmol, 95% yield). LC-MS Anal. Calc'd for C19H20FNO2 313.15, found [M+H]+ 314.1 Tr = 0.75 min (Method A
95% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; Sealed tube; Ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l- yl)acetate (WO 2016/073774, PCT/US 2015/059316 Intermediate 164E) (5 g, 17.00 mmol) was taken up in dioxane (28.3 ml) and water (7.08 ml). 4-chloro-6-fluoroquinoline (2.57 g, 14.15 mmol) was added followed by K2CO3 (5.87 g, 42.5 mmol). The reaction mixture was bubble with nitrogen gas for 5 minutes before the addition of Pd(Ph3P)4 (0.327 g, 0.283 mmol). After addition, reaction was vacated and backfilled with N2 three times and then sealed (sealed vial parafilmed) and heated to 100 C for 16 hours. The reaction was concentrated in vacuo and purified directly via silica gel flash column chromatography to give Intermediate 10A (4.22 g, 13.47 mmol, 95 % yield). LC-MS Anal. Calc'd for C19H20FNO2 313.15, found [M+H] 314.1 Tr = 0.75 min (Method A).
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; Sealed tube; Ethyl 2-(4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)cyclohex-3 -en-i - yl)acetate (Intermediate 164E) (5 g, 17.00 mmol) was taken up in dioxane (28.3 ml) and water (7.08 ml). 4-Chloro-6-fluoroquinoline (2.57 g, 14.15 mmol) was added followed by K2C03 (5.87 g, 42.5 mmol). Mixture was bubbled with nitrogen gas for 5 minutesbefore the addition of Pd(Ph3P)4 (0.327 g, 0.283 mmol). After the addition, the reaction was evacuated and backfilled with N2 three times and then sealed (sealed vial parafilmed) and heated to 100 C for 16 hours. The reaction was concentrated in vacuo and purified directly via silica gel flash colunm chromatography to give Intermediate 164F (4.22 g,13.47 mmol, 95% yield). LC-MS Anal. Calc’d for C,9H20FN02 313.15, found [M+H]314.1 T = 0.75 mm (Method A).
  • 9
  • [ 5332-24-1 ]
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(quinolin-3-yl)cyclohex-3-en-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
96% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃; for 16h;Inert atmosphere; Sealed tube; Ethyl 2-(4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)cyclohex-3 -en-i - yl)acetate (5.26 g, 17.88 mmol) was taken up in Dioxane (40 mL) and Water (10.00 mL).3 -bromoquinoline (3.1 g, 14.90 mmol) was added followed by potassium carbonate (6. 18g, 44.7 mmol). Mixture was bubble with N2 for 5 minutes before addition of tetrakis (triphenylphosphine) palladium(0) (0.344 g, 0.298 mmol). After addition, reaction was evacuated and backfilled with N2 three times and then sealed and heated to 100 C for6h. The Reaction was diluted with EtOAc and water. Organic was separated andwashed with brine, dried over MgSO4, filtered and concentrated in vacuo and purified directly via ISCO (120 g column, 85 mL/min, 0-30% EtOAc in hexanes) to give Preparation 200A (4.47 g, 14.38 mmol, 96 % yield). 1H NMR (400MHz, CHLOROFORM-d) ö 9.05 (d, J=2.3 Hz, 1H), 8.09 (d, J=8.4 Hz, 1H), 8.02 (d, J=2.2 Hz, 1H), 7.86 - 7.76 (m, 1H), 7.67 (ddd, J=8.4, 6.9, 1.5 Hz, 1H), 7.58 - 7.45 (m, 1H), 6.38 -6.18 (m, 1H), 4.20 (q, J7.1 Hz, 2H), 2.67 - 2.56 (m, 2H), 2.55 - 2.43 (m, 1H), 2.42 - 2.35 (m, 2H), 2.30 - 2.18 (m, 1H), 2.12 - 1.92 (m, 2H), 1.57 (ddt, J12.8, 10.8, 7.9 Hz, 1H), 1.36 - 1.27 (m, 3H) LC-MS: M+H=296.2 tr=0.74 mm (Method A)
  • 10
  • [ 49713-56-6 ]
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6-(trifluoromethyl)quinolin-4-yl)cyclohex-3-en-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
93% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; To a solution of <strong>[49713-56-6]4-chloro-6-(trifluoromethyl)quinoline</strong> (2.05 g, 8.85 mmol), ethyl 2-(4-(4,4,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)cyclohex-3 -en-i -yl)acetate (3.1210.62 mmol) in 1,4-dioxane (35 mL) was added potassium carbonate (3.67 g, 26.6 mmol) and water (7 mL). The reaction mixture was purged with nitrogen stream for 3 mm, followed by addition of Pd(Ph3P)4 (0.409 g, 0.354 mmol). The resulting mixture washeated at 100 °C under nitrogen stream for over night. The reaction mixture was cooled down and diluted with ethyl acetate and saturated NaHCO3 solution. The organic layer was separated and washed with sat. NaHCO3 solution, and dried over Mg504. The filtrate was concentrated in vacuo and the residue was purified via silica gel flash column chromatography, eluting with 0-50percent ethyl acetate in hexane to give Intermediate 230A(oil, 3.0 g, 8.26 mmol, 93percent yield). LC-MS Anal. Calc?d for C20H20F3N02, 363.14,found [M+H] 364.5. T = 0.97 mm (Method A). ?H NMR (400MHz, CHLOROFORM-d)8.95 (d,J=4.5 Hz, 1H), 8.31 (s, 1H), 8.22 (d,J=8.8 Hz, 1H), 7.87 (dd,J=8.8, 2.0 Hz,1H), 7.29 (d, J=4.5 Hz, 1H), 5.86 (dd, J=2.8, 1.7 Hz, 1H), 4.20 (q, J=7.2 Hz, 2H), 2.65 -2.24 (m, 5H), 2.15 - 1.96 (m, 2H), 1.73 - 1.54 (m, 2H), 1.36 - 1.29 (m, 3H)
93% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; To a solution of <strong>[49713-56-6]4-chloro-6-(trifluoromethyl)quinoline</strong> (2.05 g, 8.85 mmol), ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (3.12 g, 10.62 mmol) in 1,4-dioxane (35 mL) was added potassium carbonate (3.67 g, 26.6 mmol) and water (7 mL). The reaction mixture was purged with nitrogen stream for 3 min, followed by addition of Pd(Ph3P)4 (0.409 g, 0.354 mmol). The resulting mixture was heated at 100 °C under nitrogen stream for over night. The reaction mixture was cooled down and diluted with ethyl acetate and saturated NaHC03 solution. The organic layer was separated and washed with sat. NaHCCb solution, and dried over MgS04. The filtrate was concentrated in vacuo and the residue was purified via silica gel flash column (0288) chromatography, eluting with 0-50percent ethyl acetate in hexane to give Intermediate 11A (oil, 3.0 g, 8.26 mmol, 93percent yield). LC-MS Anal. Calc'd for C20H20F3NO2, 363.14, found [M+H] 364.5. Tr = 0.97 min (Method A). NMR (400MHz, chloroform-d) delta: 8.95 (d, J=4.5 Hz, 1H), 8.31 (s, 1H), 8.22 (d, J=8.8 Hz, 1H), 7.87 (dd, J=8.8, 2.0 Hz, 1H), 7.29 (d, J=4.5 Hz, 1H), 5.86 (dd, J=2.8, 1.7 Hz, 1H), 4.20 (q, J=7.2 Hz, 2H), 2.65 - 2.24 (m, 5H), 2.15 - 1.96 (m, 2H), 1.73 - 1.54 (m, 2H), 1.36 - 1.29 (m, 3H).
  • 11
  • [ 1166829-70-4 ]
  • [ 872365-91-8 ]
  • ethyl 2-(4-(6-(difluoromethyl)pyridin-2-yl)cyclohex-3-enyl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; In 1,4-dioxane; at 110℃; for 20h;Inert atmosphere; To the reaction mixture of <strong>[872365-91-8]2-bromo-6-(difluoromethyl)pyridine</strong> (1.55 g, 7.45 mmol), ethyl 2-(4-(4,4 ,5 ,5 -tetramethyl- 1,3 ,2-dioxaborolan-2-yl)cyclohex-3 -en-iyl)acetate (2.52 g, 8.57 mmol) in 1,4-Dioxane (20 mL) was added K2C03 (7.45 mL, 22.36 mmol) solution and the resulting mixture was purged with nitrogen stream for 3mm, followed by addition of Pd(Ph3P)4 (0.43 1 g, 0.373 mmol) and the reaction mixture was further purged with nitrogen stream and then heated at 110 C under nitrogen for 20 h. The reaction mixture was diluted with brine and ethyl acetate. The organic layer was separated, dried over MgSO4. The filtrate was concentrated in vacuo.and the residue was purified via silica gel flash column chromatography, eluting with 0-20% ethyl acetate inhexane to give Intermediate 231A (oil, 2.2 g, 7.45 mmol, 99% yield). LC-MS Anal.Calc?d for C,6H,9F2N02, 295.14, found [M+H] 296.2 . T = 1.10 mm (Method A). ?HNMR (400MHz, METHANOL-d4) oe: 7.92 - 7.80 (m, 1H), 7.60 (dd, J=8.0, 0.8 Hz, 1H),7.47 (d, J7.7 Hz, 1H), 6.71 (dd, J3.1, 2.0 Hz, 1H), 6.65 - 6.44 (m, 1H), 4.20 - 4.08 (m,2H), 2.79 - 2.65 (m, 1H), 2.56 - 2.39 (m, 2H), 2.36 (d, J=7.0 Hz, 2H), 2.20 - 1.92 (m, 3H),1.48 (dtd,J=13.0, 10.6, 5.5 Hz, 1H), 1.30- 1.22 (m, 3H)
  • 14
  • [ 1166829-70-4 ]
  • [ 1923833-60-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 7 steps 1.1: tetrakis(triphenylphosphine) palladium(0); potassium carbonate / water; 1,4-dioxane / 16 h / 100 °C / Sealed tube; Inert atmosphere 2.1: palladium on activated charcoal; ammonium formate / methanol / 1 h / Reflux 3.1: lithium hydroxide; water / ethanol / 6 h / 50 °C 4.1: triethylamine; pivaloyl chloride / tetrahydrofuran / 1.25 h / -78 - 0 °C / Inert atmosphere 4.2: 3.25 h / -78 - 20 °C 5.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.17 h / -50 °C 5.2: -50 - -20 °C 6.1: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 0 - 20 °C 7.1: propylphosphonic anhydride; pyridine / ethyl acetate / 0.08 h / 20 °C 7.2: 20 °C
Multi-step reaction with 7 steps 1: caesium carbonate; [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl)palladium(ll) dichloride / 1,4-dioxane; water / 100 °C 2: palladium on activated charcoal; hydrogen 3: lithium hydroxide / water; ethanol / 50 °C 4: triethylamine; pivaloyl chloride / tetrahydrofuran / 50 °C 5: sodium hexamethyldisilazane / tetrahydrofuran / -50 °C 6: lithium hydroxide; dihydrogen peroxide / water; tetrahydrofuran / 0 °C 7: pyridine / ethyl acetate
  • 16
  • [ 1166829-70-4 ]
  • (R)-3-((R)-2-((1s,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)propanoyl)-4-phenyloxazolidin-2-one [ No CAS ]
  • 17
  • [ 63927-22-0 ]
  • [ 1166829-70-4 ]
  • C19H21NO2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With [1,3-bis(2,6-diisopropylphenyl)imidazol-2-ylidene](3-chloropyridyl) palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 100℃; General procedure: To ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l- yl)acetate* (1.1 eq), aryl halide (1.0 eq), and Cs2C03 (2.2 eq), in 1 ,4-dioxane/water (10: 1 by volume, 0.25 M) was added catalytic amount of PEPPSI-IPr (2 mol.percent). The resulting reaction mixture was heated to 100 °C for 2-12 hours, upon which the crude reaction mixture was concentrated and loaded on silica gel. The crude reaction mixture was purified employing silica gel chromatography. * Ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate is a known compound that can be prepared from commercially available 1 ,4- dioxaspiro[4.5]decan-8-one using the procedures outlined in Barlind, J.G. et al, J. Med. Chem., 55: 10610-10629 (2012).
  • 18
  • [ 1166829-70-4 ]
  • [ 121219-03-2 ]
  • [ 1166829-64-6 ]
  • [ 1166829-66-8 ]
  • 19
  • [ 1166829-70-4 ]
  • [ 887583-90-6 ]
  • ethyl 2-(4-(2-(trifluoromethyl)pyridin-4-yl)cyclohex-3-en-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
73.4% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; A mixture of 4-bromo-2-trifiuoromcthyi)pyridine (1.5 mL, 1135 mmoi), ethyl 2-(-(4,4,5,5- tetramethyl- I ,3.2-dioxahoroian-2-yi)cvciohex-3-en- I -vl)acetate (3.44 g, Ii .69 mrnol). Na2CO3 (4.81 g, 45.4 rnmol), and Pd(Ph3P)4 (0.656 g, 0.567 mmol) in dioxane (105 mL) and water (35.0 rnL) was heated at 100 C overnight. The reaction was quenched with water and diluted with EtOAc. Layers were separaled, The aqueous phase was extracted with EtOAc (3X). The organics were combined, dried over Na2SO4, filtered, and concentrated to afford a yellow residue. Purification of the crude material by silica gel chromatography using an ISCO machine (80 g column, 60 mL/min, 0-45% EtOAc in hexanes over 27 mm, tr = 15, 23 mm) gave ethyl 2- (4-(2-(trifluorornethyl)pvridin-4-yl)cyclohex-3-en- I -vi)acetate (2.7477 g, & 33 mrnol, 73.4 % yield) as a colorless residue. ES MS (M-FI-I)± 314.1. HPLC Peak 1.03 minutes. HPLC conditions: A.
  • 20
  • [ 1166829-70-4 ]
  • [ 128071-79-4 ]
  • ethyl 2-(4-(2-fluoro-3-methylpyridin-4-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
91% With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; Sealed tube; To a reaction flask containing a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (5.93 g, 20.17 mmol) in Dioxane (120 mL) were added <strong>[128071-79-4]4-bromo-2-fluoro-3-methylpyridine</strong> (3.72 g, 19.58 mmol), Water (40.0 mL) and Na2C03 (8.30 g, 78 mmol). After the mixture was degassed with Ar for 10 min, Pd(Ph3P)4 (1.131 g, 0.979 mmol) was added. The flask was sealed and the mixture was heated to 100 C over night. The reaction mixture was cooled down and diluted with EtOAc and water, plus sonication to break up solids, then transferred to a separation funnel. The layers were separated and the aqueous layer was extracted once more with EtOAc. The organic layers were combined, washed with brine, dried over anhyd Na2S04, filtered and concentrated in vacuo to afford a white precipitate in a pale gold residue. The extract was purified via silica gel flash column chromatography, eluting with 0-25% ethyl acetate in hexane to give (0534) Intermediate 27B (gold pale oil, 5.01 g, 17.72 mmol, 91% yield). LC-MS Anal. Calc'd for C16H20FNO2 277.15, found [M+H] 278.1. Tr = 1.02 min (Method A). NMR (400MHz, chloroform-d) delta 7.94 (d, J=5.0 Hz, 1H), 6.89 (dd, J=5.1, 0.9 Hz, 1H), 5.79 - 5.49 (m, 1H), 4.18 (q, J=7.1 Hz, 2H), 2.55 - 2.28 (m, 4H), 2.26 - 2.11 (m, 5H), 2.00 - 1.86 (m, 2H), 1.55 - 1.41 (m, 1H), 1.29 (t, J=7.2 Hz, 3H).
  • 21
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(2,3-difluoropyridin-4-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
  • 22
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(3-fluoro-2-methoxypyridin-4-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
  • 23
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(3-fluoro-2-methoxypyridin-4-yl)cyclohexyl)butanoate [ No CAS ]
  • 24
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohex-3-enyl)butanoate [ No CAS ]
  • 25
  • [ 1166829-70-4 ]
  • 2-((1s,4s)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)butanoic acid [ No CAS ]
  • 26
  • [ 1166829-70-4 ]
  • 1-((1s,4s)-4-(3-(difluoromethyl)-2-methoxypyridin-4-yl)cyclohexyl)propan-1-amine [ No CAS ]
  • 27
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-2-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
  • 28
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-2-yl)cyclohexyl)butanoate [ No CAS ]
  • 29
  • [ 1166829-70-4 ]
  • 2-(4-(1-methyl-6-oxo-1,6-dihydropyridin-2-yl)cyclohexyl)butanoic acid [ No CAS ]
  • 30
  • [ 1166829-70-4 ]
  • 6-(4-(1-aminopropyl)cyclohexyl)-1-methylpyridin-2(1H)-one [ No CAS ]
  • 31
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6-methylpyridin-2-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
  • 32
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6-(trifluoromethyl)pyridin-2-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
  • 33
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6-(trifluoromethyl)pyridin-2-yl)cyclohexyl)butanoate [ No CAS ]
  • 34
  • [ 1166829-70-4 ]
  • 2-(4-(6-(trifluoromethyl)pyridin-2-yl)cyclohexyl)butanoic acid [ No CAS ]
  • 35
  • [ 1166829-70-4 ]
  • 1-(4-(6-(trifluoromethyl)pyridin-2-yl)cyclohexyl)propan-1-amine [ No CAS ]
  • 36
  • [ 1166829-70-4 ]
  • ethyl 3-ethoxy-2-(4-(6-(trifluoromethyl)quinolin-4-yl)cyclohex-3-en-1-yl)propanoate [ No CAS ]
  • 37
  • [ 1166829-70-4 ]
  • ethyl 3-ethoxy-2-(4-(6-(trifluoromethyl)quinolin-4-yl)cyclohexyl)propanoate [ No CAS ]
  • 38
  • [ 1166829-70-4 ]
  • 3-ethoxy-2-(4-(6-(trifluoromethyl)quinolin-4-yl)cyclohexyl)propanoic acid [ No CAS ]
  • 39
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6-fluoroquinolin-4-yl)cyclohex-3-en-1-yl)-3-methoxypropanoate [ No CAS ]
  • 40
  • [ 1166829-70-4 ]
  • 2-((1s,4s)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-3-methoxypropanoic acid [ No CAS ]
  • 41
  • [ 1166829-70-4 ]
  • [ 54569-28-7 ]
  • ethyl 2-(4-(1,8-naphthyridin-4-yl)cyclohex-3-en-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate; In 1,4-dioxane; water; at 100℃; A mixture of 4-bromo-l,8-naphthyridine (1.02 g, 4.88 mmol), ethyl 2-(4- (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (1.479 g, 5.03 mmol), Na2C03 (2.069 g, 19.52 mmol), and Pd(Ph3P)4 (0.282 g, 0.244 mmol) in dioxane (45.2 ml) and water (15.06 ml) was heated at 100 C ovemight. The reaction was quenched with water and diluted with EtOAc. Layers were separated. The aqueous phase was extracted with EtOAc (2X). The organics were combined, dried over Na2S04, filtered, and concentrated to afford a brown residue. Purification of the crude material by silica gel chromatography using an ISCO machine (80 g column, 60 mL/min, 0-10% MeOH in CH2CI2 over 14 min, tr = 8.5 min) gave ethyl 2-(4-(l,8-naphthyridin-4-yl)cyclohex-3-en-l- yl)acetate as an orange residue. ESI MS (M+H)+ = 297.2. HPLC Peak tr = 0.69 minutes. HPLC conditions: A
  • 42
  • [ 1166829-70-4 ]
  • [ 75-03-6 ]
  • ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
83% To the flask containing THF (136 ml) was added diisopropylamine (5.81 ml, 40.8 mmol) at -78 C, followed by addition of nBuLi (15.64 ml, 39.1 mmol). After 30 minutes, 1,3-dimethyl tetrahydropyrimidin-2(lH)-one (4.92 ml, 40.8 mmol) was added as well as a solution of ethyl 2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l- yl)acetate (10 g, 34.0 mmol) in THF (136 ml) dropwise at -78 C. The resulting mixture turned into brown and stirred at -78 C for 1 h, then iodoethane (3.26 ml, 40.8 mmol) was added slowly. After 1 hour, the reaction mixture was warmed to rt and stirred for 16 hours. The reaction mixture was quenched with water, extracted with EtOAc. The combined organics were dried with sodium sulfate, filtered, and concentrated in vacuo. The residue was dissolved in DCM, purified via silica gel flash column chromatography, eluting with 0- 40% ethyl acetate in hexane to give Intermediate 24C (colorless oil, 9.12 g, 28.3 mmol, 83% yield). LC-MS Anal. Calc'd for C18H31BO4 322.23, found [M+H] 323.3. Tr = 1.21 min (Method A). NMR (400MHz, chloroform-d) δ 6.58 - 6.47 (m, 1H), 4.21 - 4.10 (m, 2H), 2.39 - 2.00 (m, 4H), 1.96 - 1.60 (m, 5H), 1.31 - 1.22 (m, 16H), 0.88 (td, J=7.4, 2.1 Hz, 3H).
  • 43
  • [ 1166829-70-4 ]
  • [ 107-30-2 ]
  • ethyl 3-methoxy-2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)propanoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
61.1% To the flask containing THF (68.0 ml) was added LDA (1.5 M solution in hexane) (28.3 ml, 42.5 mmol) at -78 C, followed by addition of 1,3- dimethyltetrahydropyrimidin-2(lH)-one (3.07 ml, 25.5 mmol) and a solution of ethyl 2-(4- (0774) (4,4,5, 5-tetramethyl-l,3,2-dioxaborolan-2-yl)cyclohex-3-en-l-yl)acetate (WO (0775) 2016/073770) (5.0 g, 17.00 mmol) in THF (5 mL) dropwise at -78 C. The resulting mixture turned yellow. After 30 minutes chloromethyl methylether (1.936 ml, 25.5 mmol) was added slowly. The reaction mixture was stirred at -78 C for 2 hours, then the bath removed and reaction warmed to room temperature and stirred for 4 hours. The reaction was then quenched with saturated ammonium hydroxide and extracted with EtOAc. Combined organics were concentrated in vacuo and purified via silica gel flash column (0776) chromatography to give ethyl 3-methoxy-2-(4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)cyclohex-3-en-l-yl)propanoate Intermediate 51A (3.51 g, 10.38 mmol, 61.1 % yield) as a mixture of diastereomers. LC-MS Anal. Calc'd for C18H31BO5 338.23, found [M+H] 338.9, Tr = 1.06 (Method A).
  • 44
  • [ 661463-17-8 ]
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6-fluoroquinolin-4-yl)cyclohex-3-en-1-yl)acetate [ No CAS ]
  • 45
  • [ 1166829-70-4 ]
  • (R)-3-(2-((1s,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)acetyl)-4-phenyloxazolidin-2-one [ No CAS ]
  • 46
  • [ 13472-85-0 ]
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6-methoxypyridin-3-yl)cyclohex-3-en-1-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
34% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; water; at 100℃;Inert atmosphere; <strong>[1166829-70-4]ethyl 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)cyclohex-3-en-1-yl)acetate</strong> 35a (1.4g, 4.76mmol), 5-bromo-2-methoxypyridine (0.89g, 4.76mmol), sodium carbonate (1.0g, 9.52mmol) and [1,1'-bis(diphenylphosphino)ferrocene]palladium dichloride (174 mg, 0.24 mmol),1,4-dioxane (25 ml) and water (50 ml) were heated to 100 C under a nitrogen atmosphere and stirred overnight. Cooling to room temperature, the solvent was removed under reduced pressure, the residue was purified by silica gel column chromatography (petroleum ether / ethyl acetate = 10/1), To give the desired product ethyl 2-(4-(6-methoxypyridin-3-yl)cyclohex-3-en-1-yl)acetate 35b (0.45g, white solid), yield: 34%.
  • 47
  • [ 1166829-70-4 ]
  • [ 175278-11-2 ]
  • ethyl 2-(2’-bromo-4’,6’-difluoro-2,3,4,5-tetrahydro-[1,1‘-biphenyl]-4-yl)acetate [ No CAS ]
YieldReaction ConditionsOperation in experiment
86% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate; In 1,4-dioxane; at 70℃; for 20h;Sealed tube; Step 3. Ethyl 2-(2'-bromo-4',6'-difluoro-2,3,4,5-tetrahydro-[l,l'-biphenyl]-4-yl)acetate. In a sealed microwave tube, a mixture of ethyl 2-[4-(tetramethyl-l,3,2-dioxaborolan-2- yl)cyclohex-3-en-l-yl] acetate (200 mg, 0.68 mmol), [1,1'- bis(diphenylphosphino)ferrocene]dichloropalladium(II) (24.9 mg, 0.03 mmol), l-bromo-3,5- difluoro-2-iodobenzene (260 mg, 0.82 mmol) and sodium carbonate (0.85 mL, 2.0 M, 1.7 mmol) in dioxane (3.40 mL) was heated at 70C for 20 h. Upon completion of the reaction, the reaction mixture was filtered through celite, washed thoroughly with EtOAc, and purified via flash chromatography (0-20% EtOAc/heptanes) to obtain the title compound as a colorless oil (210 mg, 86%). 1H NMR (400 MHz, CDCb) d 7.13 (td, /= 2.0, 8.1 Hz, 1H), 6.78 (dt, / = 2.5, 8.8 Hz, 1H), 5.60 (d, / = 1.7 Hz, 1H), 4.17 (q, / = 7.2 Hz, 2H), 2.45 - 2.31 (m, 3H), 2.22 - 2.12 (m, 1H), 2.00 - 1.84 (m, 2H), 1.63 - 1.50 (m, 1H), 1.48 (s, 2H), 1.28 (t, / = 7.1 Hz, 3H). [M+H] = 361.0.
  • 48
  • [ 1166829-70-4 ]
  • (R)-3-(2-((1s,4S)-4-(6-fluoroquinolin-4-yl)cyclohexyl)acetyl)-4-phenyloxazolidin-2-one [ No CAS ]
  • 49
  • [ 1166829-70-4 ]
  • N-(1-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)-2-methoxyethyl)-2-(4-methoxybenzoyl)hydrazinecarboxamide [ No CAS ]
  • 50
  • [ 1166829-70-4 ]
  • 4-(4-(2-ethoxy-1-isocyanatoethyl)cyclohexyl)-6-(trifluoromethyl)quinoline [ No CAS ]
  • 51
  • [ 1166829-70-4 ]
  • N-(2-ethoxy-1-(4-(6-(trifluoromethyl)quinolin-4-yl)cyclohexyl)ethyl)-2-(4-methoxybenzoyl)hydrazine-1-carboxamide [ No CAS ]
  • 52
  • [ 1166829-70-4 ]
  • C19H21ClFNO [ No CAS ]
  • 53
  • [ 1166829-70-4 ]
  • C25H27ClFN3O [ No CAS ]
  • 54
  • [ 1166829-70-4 ]
  • C24H26ClFN4O [ No CAS ]
  • 55
  • [ 1166829-70-4 ]
  • ethyl 2-((cis)-4-(6-fluoroquinolin-4-yl)cyclohexyl)butanoate [ No CAS ]
  • 56
  • [ 1166829-70-4 ]
  • 2-((1s,4s)-4-(6-fluoroquinolin-4-yl)cyclohexyl)butanoic acid [ No CAS ]
  • 57
  • [ 1166829-70-4 ]
  • 6-fluoro-4-((cis)-4-(1-isocyanatopropyl)cyclohexyl)quinoline [ No CAS ]
  • 58
  • [ 1166829-70-4 ]
  • C27H31FN4O3*C2HF3O2 [ No CAS ]
  • 59
  • [ 1166829-70-4 ]
  • C28H31F3N4O3 [ No CAS ]
  • 60
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6,8-difluoroquinolin-4-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
  • 61
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(6,8-difluoroquinolin-4-yl)cyclohexyl)butanoate [ No CAS ]
  • 62
  • [ 1166829-70-4 ]
  • 2-(4-(6,8-difluoroquinolin-4-yl)cyclohexyl)butanoic acid [ No CAS ]
  • 63
  • [ 1166829-70-4 ]
  • C19H20F2N2O [ No CAS ]
  • 64
  • [ 1166829-70-4 ]
  • N-(1-(4-(6,8-difluoroquinolin-4-yl)cyclohexyl)propyl)-2-(4-methoxybenzoyl)hydrazine-1-carboxamide [ No CAS ]
  • 65
  • [ 159454-98-5 ]
  • [ 73183-34-3 ]
  • [ 1166829-70-4 ]
  • 66
  • [ 1166829-70-4 ]
  • 1-(4-(2,2-difluorobenzo[d][1,3]dioxol-4-yl)cyclohexyl)propan-1-amine [ No CAS ]
  • 67
  • [ 1166829-70-4 ]
  • C23H24ClF2NO3 [ No CAS ]
  • 68
  • [ 1166829-70-4 ]
  • C19H24F2O3 [ No CAS ]
  • 69
  • [ 1166829-70-4 ]
  • C19H26F2O3 [ No CAS ]
  • 70
  • [ 1166829-70-4 ]
  • 2-(4-(4-(difluoromethoxy)phenyl)cyclohexyl)butanoic acid [ No CAS ]
  • 71
  • [ 1166829-70-4 ]
  • 1-(4-(4-(difluoromethoxy)phenyl)cyclohexyl)propan-1-amine [ No CAS ]
  • 72
  • [ 1166829-70-4 ]
  • 4-chloro-N-(1-((trans)-4-(4-(difluoromethoxy)phenyl)cyclohexyl)propyl)benzamide [ No CAS ]
  • 73
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(4-methoxypyrimidin-2-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
  • 74
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(4-methoxypyrimidin-2-yl)cyclohexyl)butanoate [ No CAS ]
  • 75
  • [ 1166829-70-4 ]
  • 2-(4-(4-methoxypyrimidin-2-yl)cyclohexyl)butanoic acid [ No CAS ]
  • 76
  • [ 1166829-70-4 ]
  • 1-(4-(4-methoxypyrimidin-2-yl)cyclohexyl)propan-1-amine [ No CAS ]
  • 77
  • [ 1166829-70-4 ]
  • C21H26ClN3O2 [ No CAS ]
  • 78
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(5-methoxypyridin-3-yl)cyclohex-3-en-1-yl)butanoate [ No CAS ]
  • 79
  • [ 1166829-70-4 ]
  • ethyl 2-(4-(5-methoxypyridin-3-yl)cyclohexyl)butanoate [ No CAS ]
  • 80
  • [ 1166829-70-4 ]
  • 2-(4-(5-methoxypyridin-3-yl)cyclohexyl)butanoic acid [ No CAS ]
  • 81
  • [ 1166829-70-4 ]
  • 1-(4-(5-methoxypyridin-3-yl)cyclohexyl)propan-1-amine [ No CAS ]
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