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[ CAS No. 903550-26-5 ] {[proInfo.proName]}

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Chemical Structure| 903550-26-5
Chemical Structure| 903550-26-5
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Product Details of [ 903550-26-5 ]

CAS No. :903550-26-5 MDL No. :MFCD09037501
Formula : C14H23BN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :ZZRFDLHBMBHJTI-UHFFFAOYSA-N
M.W : 278.16 Pubchem ID :11587208
Synonyms :
Chemical Name :1-(Tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Calculated chemistry of [ 903550-26-5 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.79
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 78.16
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 : Yes
Log Kp (skin permeation) : -6.56 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 2.02
Log Po/w (WLOGP) : 1.56
Log Po/w (MLOGP) : 0.98
Log Po/w (SILICOS-IT) : 0.86
Consensus Log Po/w : 1.08

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.89
Solubility : 0.358 mg/ml ; 0.00129 mol/l
Class : Soluble
Log S (Ali) : -2.6
Solubility : 0.694 mg/ml ; 0.00249 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.9
Solubility : 0.346 mg/ml ; 0.00124 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 4.11

Safety of [ 903550-26-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 903550-26-5 ]

* 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 [ 903550-26-5 ]
  • Downstream synthetic route of [ 903550-26-5 ]

[ 903550-26-5 ] Synthesis Path-Upstream   1~6

  • 1
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  • [ 848440-23-3 ]
  • [ 1357588-10-3 ]
  • [ 449758-17-2 ]
Reference: [1] Patent: WO2012/16993, 2012, A1, . Location in patent: Page/Page column 138-139
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Reference: [1] Patent: WO2012/16993, 2012, A1, . Location in patent: Page/Page column 55-56
  • 3
  • [ 76-09-5 ]
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YieldReaction ConditionsOperation in experiment
78%
Stage #1: With n-butyllithium In tetrahydrofuran; hexanes at -78℃; for 0.0833333 h;
Stage #2: With Triisopropyl borate In tetrahydrofuran; hexanes at -78 - 20℃; for 17.5 h;
Stage #3: With water; ammonium chloride In tetrahydrofuran; hexanes
l-(Tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-l,3,2-dioxaborolan-2-yl)-lH-pyrazole (14.B.A). To a 500ml flask was added l-(tetrahydro-2H-pyran-2-yl)-lH- pyrazole 14.1.A and 100 ml of THF. The solution was cooled to -78 0C at which time butyllithium (52 ml, 83 mmole, 1.6M in hexanes) and pinacol (9.8 g, 83 mmole) were added. The reaction was stired for 5 minutes at -78 C and then triisopropyl borate (19 g, 103 mmole) was added. The reaction was slowly warmed to room temperature over 90 minutes and then stirred at room temperature for an additional 16 hours at which time the reaction was quenched with NH4Cl aq. (pH ~7-8), extracted with EtOAc, and purified by silica gel chromatography to give l-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-l,3,2- dioxaborolan-2-yl)-lH-pyrazole 14.1.B (7.2 g, 38percent yield).
Reference: [1] Tetrahedron Letters, 2006, vol. 47, # 27, p. 4665 - 4669
[2] Tetrahedron Letters, 2007, vol. 48, # 23, p. 4123 - 4126
[3] Patent: WO2010/93849, 2010, A2, . Location in patent: Page/Page column 63
  • 4
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YieldReaction ConditionsOperation in experiment
67.8%
Stage #1: With n-butyllithium In tetrahydrofuran; toluene at 0 - 5℃; Inert atmosphere; Large scale
Stage #2: at 0 - 20℃; Large scale
1-(Tetrahydro-2H-pyran-2-yl)-1H-pyrazole (5 kg), THF (7.0 1) and toluene(28 1) were mixed at room temperature (RT) under nitrogen atmosphere. The mixturewas cooled to 0°C, n-BuLi (17.9 kg, i.42 M in hexanes) was added dropwise at 0-5°C over a period of 2-3 h and the mixture was stirred at 0-5°C for 1 h. Triisopropyl borate (6.8 kg) was added dropwise at 0-5°C over a period of 45 mm. The mixture was brought to RT and stirred for i-2 h. Pinacol (3.88 kg) was added portion wise tothe mixture at RT over a period of 20-30 mm followed by stirring for 45 mm. The mixture was cooled to 0°C and acetic acid (3.9 kg) was added dropwise over a period of 30 mm at 0-5°C. The mixture was brought to RT and maintained for i2-i4 h. The mixture was then cooled to 0°C and water (20 ) was added dropwise at 0-5°C over a period of 30 mm. The mixture was brought to RT and stirred for 30 mm. The aqueouslayer was separated and extracted with toluene (20 1). The combined organic layer was washed with 10 percent NaHCO3 solution (22 1) followed by water (20 1). The organic layer was concentrated under reduced pressure below 60°C. The obtained crude compound was then co-distilled with heptane (7 1). To the residue obtained heptane (5 1) was added and the mixture was stirred at 0-5°C for i-2 h. The solid was thenfiltered, washed with cold heptane (5 1) and dried at 25-30°C for 2-3 h. Yield 6.2 kg (67.8percent), HPLC purity 99.8.
53%
Stage #1: With n-butyllithium In tetrahydrofuran; hexane at -78 - -70℃;
Stage #2: at -70 - 20℃;
Stage #3: for 0.166667 h;
Preparation of 1-(tetrahydro-2H-pyran-2-yl)-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole [(21), PG3 = tetrahydro-2H-pyran-2-yl; M = 4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl]; To a cooled (-78 0C), stirred solution of 1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazole (prepared as described in the literature: IMed.Chem. 2004, 47, 2995-3008 and JOC 2008, 73, 4309-4312) (11.8 g, 78 mmol) in anhydrous THF (200 mL), 2.5 M n-BuLi in n-hexane (40 mL, 100 mmol) was slowly added, keeping T<-70 0C. After addition the mixture was stirred at -78 0C for 1 h, then triisopropyl borate (23 mL, 100 mmol) was added dropwise, keeping T<-70 0C. After addition the mixture was let to reach room temperature in about 2 h, then a solution of 2,3-dimethyl-2,3- butandiol (12.5 g, 105 mmol) in anhydrous THF (30 mL) was added, followed after 10 min by glacial acetic acid (6 mL, 100 mmol). The colorless jelly precipitate was filtered on a thick celite pad and washed thoroughly with diethyl ether. The filtrate was concentrated to yield a colorless oil that crystallized upon addition of n-heptane. The title compound was obtained as colorless crystalline powder (14.7 g, 53percent). HPLC (254 nm): Rt: 5.81 min.1H-NMR (401 MHz, DMSO-d6) δ = 7.55 (s, 1 H) 6.7 (s, 1 H) 5.75 (m, 1 H) 4.05 (m, 1 H) 3.7 (m, 1 H) 2.5 (m, 1 H) 1.85 - 2.2 (m, 2 H) 1.4 - 1.75 (m, 3 H) 1.2 (S, 12 H). ESI (+) MS: m/z 279 (MH+).
Reference: [1] Patent: WO2016/162604, 2016, A1, . Location in patent: Page/Page column 14
[2] Patent: WO2010/10154, 2010, A1, . Location in patent: Page/Page column 147-148
  • 5
  • [ 61676-62-8 ]
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Reference: [1] Patent: WO2016/54807, 2016, A1, . Location in patent: Page/Page column 51; 52
  • 6
  • [ 76-09-5 ]
  • [ 1217902-60-7 ]
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Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 11, p. 4309 - 4312
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