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[ CAS No. 1040377-08-9 ] {[proInfo.proName]}

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Chemical Structure| 1040377-08-9
Chemical Structure| 1040377-08-9
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Product Details of [ 1040377-08-9 ]

CAS No. :1040377-08-9 MDL No. :MFCD12033564
Formula : C11H19BN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :QEHDAUWYRNEWBF-UHFFFAOYSA-N
M.W : 238.09 Pubchem ID :45788855
Synonyms :

Calculated chemistry of [ 1040377-08-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.73
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 65.93
TPSA : 56.51 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.47
Log Po/w (WLOGP) : 0.17
Log Po/w (MLOGP) : -0.24
Log Po/w (SILICOS-IT) : 0.03
Consensus Log Po/w : 0.09

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.63
Solubility : 5.56 mg/ml ; 0.0233 mol/l
Class : Very soluble
Log S (Ali) : -1.23
Solubility : 14.2 mg/ml ; 0.0595 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.25
Solubility : 1.34 mg/ml ; 0.00561 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.1

Safety of [ 1040377-08-9 ]

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 [ 1040377-08-9 ]

* 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 [ 1040377-08-9 ]
  • Downstream synthetic route of [ 1040377-08-9 ]

[ 1040377-08-9 ] Synthesis Path-Upstream   1~3

  • 1
  • [ 96-49-1 ]
  • [ 269410-08-4 ]
  • [ 1040377-08-9 ]
YieldReaction ConditionsOperation in experiment
91% With sodium hydroxide In N,N-dimethyl-formamide at 140℃; for 16 h; Intermediate 1182-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxa H-pyrazol-1 -yl]ethanolA solution of 1 ,3-dioxolan-2-one (2.496 g, 28.3 mmol), 4-(4,4,5,5-tetramethyl-1 ,3,2- dioxaborolan-2-yl)-1 H-pyrazole (5 g, 25.8 mmol) and sodium hydroxide (0.103 g, 2.58 mmol) in N,N-Dimethylformamide (DMF) (18 mL) was stirred at 140°C for 16 h. then cooled to room temperature and treated with activated charcoal (200mg). The resulting mixture was stirred at room temperature for 1 h then filtered through celite (10 g). The insoluble were washed with EtOAc (50 mL) and EtOH (50ml_). The combined filtrate and washings were concentrated in vacuo. Purification of the residue by flash chromatography on silica gel using a 50 G silica cartyridge (gradient: 0 to 40percent MeOH in DCM) gave a residue which was further purified by SP4 using a 100 G silica cartridge (eluant: 0 to 20percent MeOH in DCM) to give 2-[4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 H-pyrazol-1 - yl]ethanol (5.58 g, 23.44 mmol, 91 percent yield) as a colourless oil which was used in the next step without further purification.LCMS (method A): Retention time 0.68 min, [M+H]+ = 239.13
85% With sodium hydroxide In N,N-dimethyl-formamide for 2.5 h; Heating / reflux INTERMEDIATE 34; 2-[4-f4.4.5.5-Tetramethyl-ri.3.21dioxaborolan-2-ylVρyrazol-l-yl1-ethanol; 4-Pyrazoleboronic acid pinacol ester (0.25 g, 1.29 mmol), ethylene carbonate(0.125 g, 1.42 mmol) and sodium hydroxide (5 mg, 0.13 mmol) were dissolved in DMF (1 mL) and the reaction mixture was heated to reflux for 2 Vi h. It was cooled to r.t. before addition of activated charcoal (25 mg). The resulting suspension was stirred at r.t. for Ih and then filtered through celite, washed with DMF (6 mL) and concentrated in vacuo to give the title compound (0.26g, 85percent) as a yellow oil. LCMS (ES+) 239.18 (M+H)+.
76% With caesium carbonate In N,N-dimethyl-formamide at 140℃; for 0.5 h; 100 mg of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole and 91 mg of 1,3-dioxolan-2-one weredissloved in 2 ml of dimethylformamide. 336 mg of cesium carbonate was heated to 140 °C, stirred for 0.5 h and thencooled to room temperature and concentrated. The residue was purified by column chromatography (ethyl acetate:petroleum ether = 30: 70) to give 93 mg of 2-(4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl)ethanol aspale yellow oil. Yield: 76percent.1H NMR (300 MHz, DMSO-d6) δ (ppm): 1.25 (s, 12H), 3.71 (q, J= 5.4 Hz, 2H), 4.15 (t, J = 5.4 Hz, 2H), 4.87 (t, J = 5.4Hz, 1H), 7.57 (s, 1H), 7.88 (s, 1H).
7.53 g With sodium hydroxide In N,N-dimethyl-formamide at 140℃; A solution of I ,3-dioxolan-2-one (1 .902 mL, 28.5 mmol), 4-(4,4,5,5-tetramethyl-1 ,3,2-dioxaborolan-2- yl)-IH-pyrazole (5.0239 g, 25.9 mmol) and sodium hydroxide (0.0998 g, 2.495 mmol) in N,Ndimethylformamide (DMF) (20 mL) was heated to 140 °C overnight. The mixture was cooled down to rt and then activated charcoal (200 mg) was added and this was stirred for 4 h before filtering through celite cartridge (10 g). The mixture was washed with EtOAc (50 mL) and EtCH (50 mL andthe combined filtrate was concentrated in vacuo to afford 7.53 g of brown oil. This was used crude in further reactions. LCMS: Not recorded.

Reference: [1] Patent: WO2011/54841, 2011, A1, . Location in patent: Page/Page column 107
[2] Patent: WO2008/44022, 2008, A1, . Location in patent: Page/Page column 35
[3] Patent: EP3112351, 2017, A1, . Location in patent: Paragraph 0041
[4] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 9, p. 3208 - 3212
[5] Patent: WO2010/19899, 2010, A1, . Location in patent: Page/Page column 155
[6] Patent: US2010/144783, 2010, A1, . Location in patent: Page/Page column 15
[7] Patent: US2011/281842, 2011, A1, . Location in patent: Page/Page column 45
[8] Patent: US2011/281868, 2011, A1, . Location in patent: Page/Page column 21
[9] Patent: US2012/208798, 2012, A1, . Location in patent: Page/Page column 48
[10] Patent: WO2014/140076, 2014, A1, . Location in patent: Page/Page column 208
  • 2
  • [ 214614-81-0 ]
  • [ 1040377-08-9 ]
YieldReaction ConditionsOperation in experiment
26.6%
Stage #1: With potassium acetate In N,N-dimethyl-formamide for 0.166667 h;
Stage #2: at 80℃;
To a solution of 22b (0.45g, 2.36mmol) and bis(pinacolato)diboron (0.718g, 2.83mmol) in DMF (2OmL), was added KOAc (0.694g, 7.08mmol). The mixture was 0 degassed with N2, stirred for 1 Omin and added Pd(dppf)Cl2 (58mg, 0.071 mmol). The mixture was degassed with N2 and stirred at 8O0C overnight. DMF was removed and the residue was purified by column chromatography (EA:PE=1 :10) to afford of 22c (149mg, 26.6percent yield).
Reference: [1] Patent: WO2008/88881, 2008, A1, . Location in patent: Page/Page column 47
[2] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 21, p. 6804 - 6820
  • 3
  • [ 269410-08-4 ]
  • [ 540-51-2 ]
  • [ 1040377-08-9 ]
YieldReaction ConditionsOperation in experiment
63% With caesium carbonate In N,N-dimethyl-formamide at 70℃; 4-(4,4,5,5-Tetramethyl-1 ,3,2-dioxaborolan-2-yl)-1 /-/-pyrazole (1 .00 g, 5.15 mmol) and cesium carbonate (5.04 g, 15.47 mmol) were suspended in 10 mL of dimethylformamide. 2-Bromoethanol (0.73 mL, 10.30 mmol) was added and the mixture was stirred at 70 °C for 3 hours. Additional amounts of cesium carbonate (5.04 g, 15.47 mmol) and 2-bromoethanol (0.73 mL, 10.30 mmol) were added and the mixture was left at 70 °C overnight. The solvent was evaporated under reduced pressure and the residue was partitioned between water and ethyl acetate. The organic layer was washed with water and brine, dried over magnesium sulphate, filtered and the solvent was evaporated to give 770 mg (63percent yield) of a yellowish oil that was used in the next step without further purification.LRMS (m/z): 239 (M+1 )+.
31.47% With caesium carbonate In N,N-dimethyl-formamide at 100℃; for 48 h; Inert atmosphere; Sealed Step A: Preparation of 2-(4-(4 A5 ,5-tetramethyl- 1 ,3 ,2-dioxaborolan-2-yl)- 1 H- pyrazol- 1 -yDethanol : To a flask charged with 4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2- yl)-lH-pyrazole (1.000 g, 5.154 mmol), Cs2C03 (2.687 g, 8.246 mmol), and 2-bromoethanol (0.5479 mL, 7.730 mmol) was added 10 mL of DMF and the flask was sealed under nitrogen and heated to 100 °C for 48 hours. The reaction was diluted with ethyl acetate (100 mL) and stirred for 30 minutes before it was passed through a glass microfiber filter and the cake was washed with ethyl acetate. The organic was concentrated under reduced pressure. The crude was then purified by silica gel chromatography eluting with a gradient of 75-100percent ethyl acetate in Hexanes to afford 2-(4-(4,4,5,5-tetramethyl-l ,3,2-dioxaborolan-2-yl)-lH-pyrazol- l-yl)ethanol (0.4290 g, 1.622 mmol, 31.47percent yield). MS (apci) m/z = 239.2 (M+H).
Reference: [1] Patent: WO2014/60432, 2014, A1, . Location in patent: Page/Page column 129
[2] Patent: WO2011/130146, 2011, A1, . Location in patent: Page/Page column 82-83
[3] Patent: US2014/121200, 2014, A1, . Location in patent: Paragraph 0281; 0282; 0283
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