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Chemical Structure| 1029716-44-6
Chemical Structure| 1029716-44-6
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Product Details of [ 1029716-44-6 ]

CAS No. :1029716-44-6 MDL No. :MFCD11857753
Formula : C13H23BN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :IZKVGEWCELXYRI-UHFFFAOYSA-N
M.W : 266.14 Pubchem ID :46736798
Synonyms :

Calculated chemistry of [ 1029716-44-6 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.77
Num. rotatable bonds : 4
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 75.47
TPSA : 45.51 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) : -6.6 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 1.87
Log Po/w (WLOGP) : 1.41
Log Po/w (MLOGP) : 0.72
Log Po/w (SILICOS-IT) : 0.74
Consensus Log Po/w : 0.95

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.6
Solubility : 0.67 mg/ml ; 0.00252 mol/l
Class : Soluble
Log S (Ali) : -2.45
Solubility : 0.95 mg/ml ; 0.00357 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.98
Solubility : 0.279 mg/ml ; 0.00105 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.89

Safety of [ 1029716-44-6 ]

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 [ 1029716-44-6 ]

* 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 [ 1029716-44-6 ]
  • Downstream synthetic route of [ 1029716-44-6 ]

[ 1029716-44-6 ] Synthesis Path-Upstream   1~8

  • 1
  • [ 1029716-44-6 ]
  • [ 269410-08-4 ]
YieldReaction ConditionsOperation in experiment
94% With hydrogenchloride; 2,3-dimethyl-2,3-butane diol In water at 10 - 25℃; for 4.083 h; 1 -( 1 -Ethoxyethyl)-4-(4,4,5,5-tetramethyl- 1 ,3,2-dioxaborolan-2-yl)-l H-pyrazole (60.00 g, 224 mmol) is combined with CPME (120 mL) and 2,3-dimethylbutane-2,3-dtol (26.49 g, 224 mmol). The reaction is cooled to 5-10 °C then a solution of anhydrous HQ in CPME (3.1 M, 86.8 mL, 269 mmol) is added over 15 minutes, followed by additional CPME (15 mL). The reaction is stirred at 20-25 °C and monitored for completion. After 7 hours, additional HCI solution (3 mL, 9.3 mmol) is added to the reaction and stirring is continued for an additional 15 hours to give 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2- yl)-l H-pyrazole hydrochloride salt, which is not isolated.mL) is added over 10 minutes. The reaction mixture temperature increases to 20 °C following the addition. Additional CPME (10 mL) is added and the reaction mixture is stirred for 15 minutes then cooled in an ice bath. After 3 hours the reaction mixture is filtered and the solid (triethylamine hydrochloride) is washed with cold CPME (3 x 60 mL). The filtrate and washes are combined to give 426 g of solution containing 102,3 mg of 4- (4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazo]e/g solution (total 8.15 g, 94percent )yield of 4-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyTazole) which is used directly in the next step.
77.3% With hydrogenchloride; 2,3-dimethyl-2,3-butane diol In tert-butyl methyl ether; 1,2-dichloro-ethane at 0 - 20℃; Large scale 4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1) [0166] To a mixture of 2,3-dimethylbutane-2,3-diol (25.0 kg, 211.6 mol) and 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (24, 55.0 kg, 206.7 mol) in 1,2-dichloroethane (750 kg) was slowly added a solution of HCl in MTBE (25.0 kg, 20-30percent of HCl) at 0-5° C. The resulting reaction mixture was then stirred at 10-20° C. for 3-5 hours. After the selective deprotection reaction was complete as monitored by HPLC (1: below 1percent), the reaction mixture was degassed and refilled with nitrogen before being cooled to −15° C. The cooled reaction mixture was then added triethylamine (TEA, 30.0 kg, 296.5 mol) to adjust pH to 7-8. The mixture was then gradually warmed to ambient temperature before being treated with water (150 kg). The two phases were separated and the organic layer was washed with brine (60 kg) and dried over sodium sulfate (Na2SO4). The drying reagent, sodium sulfate (Na2SO4), was removed by filtration and the resulting solution was concentrated under reduced pressure at 40-50° C. to a thick oil. The residue was warmed to 60-70° C. and diluted with petroleum ether (100 kg) at the same temperature. The resulting mixture was then gradually cooled to ambient temperature and subsequently to −5° C. and stirred at the same temperature for 3 hours. The solids was collected by centrifugation and dried at 50-60° C. under vacuum to afford the crude desired product (1, 33.75 kg, 40.11 kg theoretical, 84.1percent). The crude desired product was then suspended in 1,2-dichloroethane (30 kg) and the resulting mixture was heated to reflux until a clear solution was formed. To the hot solution was then added petroleum ether (150 kg) at the same temperature. The resulting mixture was then gradually cooled to ambient temperature and subsequently to −5° C. and stirred and the same temperature for 3 hours. The solids were collected by centrifugation and dried under vacuum at 50-60° C. to afford 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1, 31.0 kg, 40.11 kg theoretical, 77.3percent) as an off-white solid, which is identical in every comparable aspect to the material synthesized by the synthetic method as described above in Example 5.
Reference: [1] Patent: WO2016/205487, 2016, A1, . Location in patent: Page/Page column 27-28
[2] Patent: US2014/256941, 2014, A1, . Location in patent: Paragraph 0166
  • 2
  • [ 1024120-52-2 ]
  • [ 1195-66-0 ]
  • [ 1029716-44-6 ]
YieldReaction ConditionsOperation in experiment
99%
Stage #1: With isopropyl magnesium chloride - lithium chloride complex In tetrahydrofuran at 20 - 25℃; for 16 h;
Stage #2: at -20 - 25℃; for 2 h;
Step 3[00251j To an oven-dried vial was charged a solution of isopropyl magnesium /lithium chloride solution (1.0 M in THF) (6.32 ml, 8.22 mmol) at room temperature, andto this solution was added 4-bromo-1-(1-ethoxyethyl)-1H-pyrazole (1.00 g, 4.56 mmol)dropwise and the resulting mixture was stirred at room temperature for 16 h. Theresulting solution was then cooled to -20 °C and 2-methoxy-4,4,5,5-tetramethyl-1,3,2- dioxaborolane (1.73 1 g, 10.95 mmol) was added via syringe and the resulting mixture was allowed to warm to rt. After 2h at room temperature, the reaction was quenched by addition of aq. sat. ammonium chloride (15 mL) causing a white precipitate to form.After diluting with additional water (20 mL), the mixture was extracted with hexanes (140 mL x 2) and the combined extracts were washed with aq. sat. sodium bicarbonate, brine, then dried over sodium sulfate, filtered and concentrated to afford 1.20 g (99percent) of the product as a colorless oil
99%
Stage #1: With TurboGrignard In tetrahydrofuran at 20℃;
Stage #2: at -20 - 20℃; for 2 h;
Step 3 To an oven dried vial was charged a solution of isopropylmagnesium chloride - lithium chloride complex (1.0 M in THF) (6.32 ml, 8.22 mmol) at rt, and 4-bromo-l-(l- ethoxyethyl)-lH-pyrazole from Step 2 (1.00 g, 4.56 mmol) was added dropwise and the resulting mixture was stirred at rt overnight. The solution obtained was then cooled to -20 °C and 2-methoxy-4,4,5,5-tetramethyl-l,3,2-dioxaborolane (1.731 g, 10.95 mmol) was added dropwise via syringe. After the addition was complete, the reaction was allowed to slowly warm to rt and stir at rt for 2 h. The reaction was quenched at this time by the addition of aq. sat. NH4C1 (15 mL) which caused a white precipitate to form. Water was added (20 mL) and the mixture was extracted with hexanes (140 mL x 2). The combined extracts were washed with aq. sat. sodium bicarbonate, brine, then dried over anhyd sodium sulfate, filtered and concentrated to afford 1.20 g (99percent) of the desired product as a colorless oil. 1H NMR (400MHz, chloroform-d) δ 7.91 (s, 1H), 7.79 (s, 1H), 5.55 (q, J=5.9 Hz, 1H), 3.51 - 3.39 (m, 1H), 3.37 - 3.25 (m, 1H), 1.67 (d, J=5.9 Hz, 3H), 1.37 - 1.30 (m, 12H), 1.15 (t, J=7.0 Hz, 3H).
99%
Stage #1: With TurboGrignard In tetrahydrofuran at 20℃;
Stage #2: at -20 - 20℃; for 2 h;
A solution of isopropylmagnesium chloride-lithium chloride complex (1.0 M in THF) (6.32 ml, 8.22 mmol) was charged to the dried flask under rt,And 4-bromo-1- (1-ethoxyethyl) -1H-pyrazole (1.00 g, 4.56 mmol) from step 2 was added dropwise and the resulting mixture was stirred overnight at rt. The resulting solution was then cooled to -20 ° C and 2-methoxy-4,4,5,5-tetramethyl-1,3,2-dioxaborolane was added dropwise via syringe (1.731 g, 10.95 mmol). After the addition was complete, the reaction was slowly warmed to rt and stirred at rt for 2 h. The reaction was quenched by the addition of saturated aqueous NH4Cl (15 mL) to form a white precipitate. Water (20 mL) was added and the mixture was extracted with hexane (140 mL x 2). The combined extracts were washed with saturated aqueous sodium bicarbonate, brine, then dried over anhydrous sodium sulfate, filtered and concentrated to afford 1.20 g (99percent) of the desired product as a colorless oil.
56.4%
Stage #1: at 20℃; for 12 h;
Stage #2: at -20 - 10℃;
1-(Ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (19).; To a 100 ml solution of iPrMgCl.LiCl (50 mmol, 1.8 equiv) was added 4-bromo-1-(ethoxyethyl)-1H-pyrazole (22, 6.15 g, 28 mmol) at room temperature. The resulting reaction mixture was stirred at room temperature for 12 hrs and then cooled to -20° C. Methoxy pinacolborate (23, 10.6 g, 67 mmol, 2.4 equiv) was then added to the reaction mixture. The resulting mixture was stirred at 0-10° C. for 1 h. Aqueous NH4Cl was added to quench the reaction. The mixture was then extracted with petroleum ether (PE). The combined PE extracts were washed with saturated NaHCO3, dried over Na2SO4 and concentrated under reduced pressure. The crude product was crystallized in PE to afford 1-(ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (19, 4.2 g, 7.45 g theoretical, 56.4percent yield) as a white to off-white solid (GC purity: 99percent). For 19: 1H NMR (DMSO-d6, 400 MHz) δ ppm 8.09 (s, 1H), 8.58 (s,1H), 7.62 (s,1H), 5.55 (q, 1H, J=6.1 Hz), 3.37 (dq, 1H, J=7.1, 9.6 Hz), 3.12 (dq, 1H, J=7.0, 9.7 Hz), 1.56 (d, 3H, J=6.0 Hz), 1.24 (s, 12H), 1.00 (t, 3H, J=7.0 Hz); C13H23BN2O3 (MW, 266.14), LCMS (EI) m/e 267 (M++H).
56.4%
Stage #1: With TurboGrignard In tetrahydrofuran at 20℃; for 12 h;
Stage #2: at -20 - 10℃; for 1 h;
Stage #3: With water; ammonium chloride In tetrahydrofuran
1-(Ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (24) [0165] To a 100 ml solution of iPrMgCl.LiCl (50 mmol, 1.8 equiv) in THF was added 4-bromo-1-(ethoxyethyl)-1H-pyrazole (6.15 g, 28 mmol) at ambient temperature. The resulting reaction mixture was stirred at ambient temperature for 12 h and then cooled to −20° C. Methoxy pinacolborate (10.6 g, 67 mmol, 2.4 equiv) was then added to the reaction mixture at −20° C. The resulting mixture was stirred at 0-10° C. for 1 h. Aqueous NH4Cl was added to quench the reaction. The mixture was then extracted with petroleum ether (PE). The combined PE extracts were washed with saturated NaHCO3, dried over Na2SO4 and concentrated under reduced pressure. The crude product was crystallized in PE to afford 1-(ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (24, 4.2 g, 7.45 g theoretical, 56.4percent yield) as a white to off-white solid (GC purity: 99percent). For 24: 1H NMR (DMSO-d6, 400 MHz) δ 8.09 (s, 1H), 8.58 (s, 1H), 7.62 (s, 1H), 5.55 (q, 1H, J=6.1 Hz), 3.37 (dq, 1H, J=7.1, 9.6 Hz), 3.12 (dq, 1H, J=7.0, 9.7 Hz), 1.56 (d, 3H, J=6.0 Hz), 1.24 (s, 12H), 1.00 (t, 3H, J=7.0 Hz) ppm; C13H23BN2O3 (MW, 266.14), LCMS (EI) m/e 267 (M++H).

Reference: [1] Patent: WO2014/74661, 2014, A1, . Location in patent: Paragraph 00251
[2] Patent: WO2015/69310, 2015, A1, . Location in patent: Paragraph 00175
[3] Patent: TWI582077, 2017, B, . Location in patent: Page/Page column 82
[4] Organic Letters, 2009, vol. 11, # 9, p. 1999 - 2002
[5] Patent: US2010/190981, 2010, A1, . Location in patent: Page/Page column 105
[6] Patent: US2014/256941, 2014, A1, . Location in patent: Paragraph 0166
  • 3
  • [ 1024120-52-2 ]
  • [ 73183-34-3 ]
  • [ 1029716-44-6 ]
YieldReaction ConditionsOperation in experiment
68.5% With potassium acetate In 1,4-dioxane at 50℃; for 16 h; Inert atmosphere 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (11-II)To a solution of compound 11-II-a (600 mg, 2.73 mmol) in dioxane (15 mL) was added KOAc (800 mg, 8.2 mmol), bis(pinacolato)diboran (1.39 g, 5.4 mmol) and Pd(dppf)Cl2 (0.06 g, 0.08 mmol) at RT. The reaction mixture was degassed by purging with argon for 30 minutes and stirred at 50° C. for 16 h. After completion of the reaction (monitored by TLC), the reaction was quenched with H2O and extracted with EtOAc (3.x.100 mL). The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo. The crude compound was purified by column chromatography (15percent EtOAc/Hexane) to afford 11-II (500 mg, 68.5percent) as off white solid. TLC: 30percent EtOAc/Hexane (Rf: 0.4); 1H-NMR (CDCl3, 200 MHz): δ 7.90 (s, 1H), 7.79 (s, 1H), 5.56 (q, J=6.0 Hz, 1H), 3.55-3.25 (m, 2H), 1.63 (d, J=6.0 Hz, 3H), 1.35 (s, 12H), 1.15 (t, J=7.2 Hz, 3H); Mass: 267 [M++1].
68.5% With potassium acetate In 1,4-dioxane 1-(1-ethoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (5-II)
To a solution of compound 5-II-a (600 mg, 2.73 mmol) in dioxane (15 mL) was added KOAc (800 mg, 8.2 mmol), bis(pinacolato)diboran (1.39 g, 5.4 mmol) and Pd(dppf)Cl2 (0.06 g, 0.08 mmol) at RT.
The reaction mixture was degassed by purging with argon for 30 minutes and stirred at 50° C. for 16 h.
After completion of the reaction (monitored by TLC), the reaction was quenched with H2O and extracted with EtOAc (3*100 mL).
The combined organic layers were dried over anhydrous Na2SO4 and concentrated in vacuo.
The crude compound was purified by column chromatography (15percent EtOAc/Hexane) to afford 5-II (500 mg, 68.5percent) as off white solid. TLC: 30percent EtOAc/Hexane (Rf: 0.4); 1H-NMR (CDCl3, 200 MHz): δ 7.90 (s, 1H), 7.79 (s, 1H), 5.56 (q, J=6.0 Hz, 1H), 3.55-3.25 (m, 2H), 1.63 (d, J=6.0 Hz, 3H), 1.35 (s, 12H), 1.15 (t, J=7.2 Hz, 3H); Mass: 267 [M++1].
Reference: [1] Patent: US2011/230476, 2011, A1, . Location in patent: Page/Page column 293
[2] Patent: US2011/269244, 2011, A1, . Location in patent: Page/Page column
  • 4
  • [ 61676-62-8 ]
  • [ 575452-22-1 ]
  • [ 1029716-44-6 ]
YieldReaction ConditionsOperation in experiment
85.1%
Stage #1: With isopropylmagnesium chloride In tetrahydrofuran at -15 - -5℃; for 1.25 h; Inert atmosphere
Stage #2: at -5 - 16℃; for 0.75 h; Inert atmosphere
1-(Ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (19). A 22 L 4-neck flask equipped with a mechanical stirrer, thermowell, addition funnel, and N2 inlet was charged with 1-(ethoxyethyl)-4-iodo-1H-pyrazole (20, 700.0 g, 2.63 mol) and THF (5.5 L). The resulting solution was cooled to between -12° C.--15° C. A solution of 2 M i-PrMgCl in THF (1513 mL, 3.03 mol, 1.15 equiv) was added via an addition funnel over 30 min while maintaining the reaction temperature at <-5° C. and the tan suspension was stirred at <-5° C. for 0.75 hr. The resulting reaction mixture was further cooled to -15° C. and 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane (16, 734 g, 805 mL, 3.95 mol, 1.5 equiv) was added rapidly via an addition funnel with the reaction temperature increasing to -5°. [Note: previous work with the analogous TMS-protected pyrazole has shown that slow addition of 2-isopropoxy-4,4,5,5-tetramethyl[1,3,2]dioxaborolane results in a lower yield.] A nearly clear light brown solution was developed followed by reformation of grayish light suspension. The cooling bath was then removed and the reaction mixture was allowed to warm to 16° C. over 0.75 hr. The mixture was poured into 50 L reparatory funnel containing a stirred saturated aqueous NH4Cl solution (4 L). The mixture was diluted with toluene (8 L), heptane (8 L) and H2O (2 L). The aqueous phase was removed and the organic phase was washed with warm (30° C.) H2O (4.x.3 L) and saturated brine (2.x.3 L). The organic phase was dried over Na2SO4, and the solvents weree removed under reduced pressure. The residual toluene was further removed by co-evaporation with heptane (2 L). The residual oil was transferred to a 4 L beaker using a minimum amount of heptane (100 mL) and scratched to induce crystallization. The solid was filtered, washed with heptane (200 mL) and dried overnight in a vacuum oven at 30-40° C. The filtrate was concentrated under reduced pressure and the residue was allowed to stand overnight. The resulting solid was filtered, washed with heptane (100 mL) and dried overnight in a vacuum oven at 30-40° C. The two crops were combined to afford 1-(ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (19, 596 g, 700 g theoretical, 85.1percent) as a white to off-white solid. For 19: 1H NMR (DMSO-d6, 400 MHz) δ ppm 8.09 (s, 1H), 8.58 (s,1H), 7.62 (s,1H), 5.55 (q, 1H, J=6.1 Hz), 3.37 (dq, 1H, J=7.1, 9.6 Hz), 3.12 (dq, 1H, J=7.0, 9.7 Hz), 1.56 (d, 3H, J=6.0 Hz), 1.24 (s, 12H), 1.00 (t, 3H, J=7.0 Hz); C13H23BN2O3 (MW, 266.14), LCMS (EI) m/e 267 (M++H).
Reference: [1] Organic Letters, 2009, vol. 11, # 9, p. 1999 - 2002
[2] Patent: US2010/190981, 2010, A1, . Location in patent: Page/Page column 104
  • 5
  • [ 269410-08-4 ]
  • [ 109-92-2 ]
  • [ 1029716-44-6 ]
YieldReaction ConditionsOperation in experiment
97.3%
Stage #1: With hydrogenchloride In 1,4-dioxane; toluene at 35 - 40℃; Inert atmosphere
Stage #2: With sodium hydrogencarbonate In 1,4-dioxane; toluene for 1 h;
1-(Ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (19).; A 22 L 4-neck flask equipped with a mechanical stirrer, thermowell, addition funnel, condenser and N2 inlet was charged with 4-(4,4,5,5-tetra-methyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (17, 1.42 kg, 7.32 mol), toluene (9.5 L) and ethyl vinyl ether (18, 790.5 g, 1050 mL, 10.98 mol, 1.50 equiv). A 4 M HCl in dioxane (50 mL) was added via an addition funnel over 10 minutes and the resulting reaction mixture was heated at 35-40° C. for 7 hr to give a clear homogeneous solution. When the reaction was shown to be complete by GC, solid NaHCO3 (130 g) was added and the mixture was stirred for 1 hr before being filtered. The filtrate was concentrated under reduced pressure. Heptane (200 mL) was added to the residue to affect crystallization. The solid was collected by filtration and dried in a vacuum oven to afford 1-(ethoxyethyl)-4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazole (19, 1.896 Kg, 1.948 Kg theoretical, 97.3percent) as a white to off-white solid. For 19: 1H NMR (DMSO-d6, 400 MHz) δ ppm 8.09 (s, 1H), 8.58 (s,1H), 7.62 (s,1H), 5.55 (q, 1H, J=6.1 Hz), 3.37 (dq, 1H, J=7.1, 9.6 Hz), 3.12 (dq, 1H, J=7.0, 9.7 Hz), 1.56 (d, 3H, J=6.0 Hz), 1.24 (s, 12H), 1.00 (t, 3H, J=7.0 Hz); C13H23BN2O3 (MW, 266.14), LCMS (EI) m/e 267 (M++H).
Reference: [1] Patent: US2010/190981, 2010, A1, . Location in patent: Page/Page column 103-104
[2] Journal of Medicinal Chemistry, 2017, vol. 60, # 20, p. 8336 - 8357
[3] Bioorganic and Medicinal Chemistry Letters, 2018, vol. 28, # 8, p. 1357 - 1362
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  • [ 1029716-44-6 ]
Reference: [1] Patent: WO2016/11930, 2016, A1, . Location in patent: Page/Page column 163
  • 7
  • [ 73183-34-3 ]
  • [ 575452-22-1 ]
  • [ 1029716-44-6 ]
Reference: [1] Patent: WO2016/90285, 2016, A1, . Location in patent: Paragraph 00367
  • 8
  • [ 941685-26-3 ]
  • [ 1029716-44-6 ]
  • [ 941685-27-4 ]
Reference: [1] Patent: US2011/224190, 2011, A1, . Location in patent: Page/Page column 37-38
[2] Patent: US2015/246046, 2015, A1, . Location in patent: Paragraph 0133
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[ 1301198-65-1 ]

1-(Methoxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.86

Chemical Structure| 1072944-26-3

[ 1072944-26-3 ]

4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Similarity: 0.85

Chemical Structure| 847818-70-6

[ 847818-70-6 ]

1-Ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.83

Chemical Structure| 847818-71-7

[ 847818-71-7 ]

1-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.82

Ethers

Chemical Structure| 1301198-65-1

[ 1301198-65-1 ]

1-(Methoxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.86

Chemical Structure| 847818-71-7

[ 847818-71-7 ]

1-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.82

Chemical Structure| 1000801-76-2

[ 1000801-76-2 ]

1-(3-Methoxypropyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.82

Chemical Structure| 847818-59-1

[ 847818-59-1 ]

(1-(2-Methoxyethyl)-1H-pyrazol-4-yl)boronic acid

Similarity: 0.64

Chemical Structure| 1052686-60-8

[ 1052686-60-8 ]

2-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrimidine

Similarity: 0.51

Related Parent Nucleus of
[ 1029716-44-6 ]

Pyrazoles

Chemical Structure| 1003846-21-6

[ 1003846-21-6 ]

1-(Tetrahydro-2H-pyran-2-yl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.92

Chemical Structure| 1301198-65-1

[ 1301198-65-1 ]

1-(Methoxymethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.86

Chemical Structure| 1072944-26-3

[ 1072944-26-3 ]

4-(5,5-Dimethyl-1,3,2-dioxaborinan-2-yl)-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole

Similarity: 0.85

Chemical Structure| 847818-70-6

[ 847818-70-6 ]

1-Ethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.83

Chemical Structure| 847818-71-7

[ 847818-71-7 ]

1-(2-Methoxyethyl)-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Similarity: 0.82