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[ CAS No. 1006875-83-7 ] {[proInfo.proName]}

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Chemical Structure| 1006875-83-7
Chemical Structure| 1006875-83-7
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Product Details of [ 1006875-83-7 ]

CAS No. :1006875-83-7 MDL No. :MFCD22570725
Formula : C15H25BN2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :UZSRXQQCEWMKJL-UHFFFAOYSA-N
M.W : 308.18 Pubchem ID :59216326
Synonyms :

Calculated chemistry of [ 1006875-83-7 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.73
Num. rotatable bonds : 5
Num. H-bond acceptors : 5.0
Num. H-bond donors : 0.0
Molar Refractivity : 85.32
TPSA : 62.58 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) : 2.23
Log Po/w (WLOGP) : 1.52
Log Po/w (MLOGP) : 0.74
Log Po/w (SILICOS-IT) : 0.91
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) : -2.99
Solubility : 0.313 mg/ml ; 0.00101 mol/l
Class : Soluble
Log S (Ali) : -3.18
Solubility : 0.204 mg/ml ; 0.000662 mol/l
Class : Soluble
Log S (SILICOS-IT) : -3.3
Solubility : 0.155 mg/ml ; 0.000502 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.49

Safety of [ 1006875-83-7 ]

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 [ 1006875-83-7 ]

* 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 [ 1006875-83-7 ]
  • Downstream synthetic route of [ 1006875-83-7 ]

[ 1006875-83-7 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 269410-08-4 ]
  • [ 5292-43-3 ]
  • [ 1006875-83-7 ]
YieldReaction ConditionsOperation in experiment
85% With potassium carbonate In acetone at 65℃; for 13 h; Inert atmosphere A mixture of 4-(4,4, 5, 5-tetramethyl- 1,3 ,2-dioxaborolan-2-yl)- 1 H-pyrazole (2.0 g, 10.31 mmol), tert-butyl 2-bromoacetate (2.212 g, 11.34 mmol) and K2C03 (1.709 g, 12.37 mmol) in acetone (20 mL) was stirred at 65 °C for 13 hours under nitrogen. The reaction was poured into ice water (20 mL) and extracted with ethyl acetate (50 mL x 2). The combined organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (petroleum ether/ethyl acetate = 5/1) to give the title compound (3 g, 8.76 mmol, 85 percent yield) as an oil. LCMS (Method C): m/z 309.2 (M+H), retention time: 1.946 minutes; ‘H NIVIR (400 MHz, CDC13) ö 7.82 (s, 1H), 7.75 (s, 1H), 4.82 (s, 1H), 1.47 (s, 9H), 1.28 (s, 12H).
84% With caesium carbonate In N,N-dimethyl-formamide at 90℃; To a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.5 g, 0.0077 mol) in DMF (25 mL) was added 2-bromoacetic acid 1,1-dimethylethyl ester (1.2 mL, 0.0085 mol) and cesium carbonate (3.8 g, 0.012 mol).
The suspension was stirred at 90° C. overnight.
The reaction mixture was cooled to RT and partitioned with ethyl acetate and water.
The organic layer was washed with water, brine, and dried over MgSO4.
The solution was concentrated to afford the desired compound (2.0 g, 84percent).
Analytical LC/MS: (M+H)+=309.4.
81%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 0.0833333 h;
Stage #2: at 0 - 20℃; for 2 h;
1.0 M Potassium tert-butoxide in THF (2.4 mL, 2.4 mmol) was added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.39 g, 2.0 mmol) in N,N-dimethylformamide (6.0 mL) at 0° C. The reaction mixture was stirred at room temperature for 5 min. After cooled to 0° C., to the mixture was added t-butyl bromoacetate (0.5 mL, 3 mmol). The reaction was stirred at room temperature for 2 h, then diluted with ethyl acetate, washed with sat. NaHCO3, water, brine, dried over Na2SO4, filtered and concentrated. The product (0.5 g, 81percent) was purified by chromatography eluting with hexanes/EtOAc (max. EtOAc 30percent). LCMS calculated for C15H26BN2O4 (M+H)+: m/z=309.2; Found: 309.1
81%
Stage #1: With potassium <i>tert</i>-butylate In tetrahydrofuran; N,N-dimethyl-formamide at 0 - 20℃; for 0.0833333 h;
Stage #2: at 0 - 20℃; for 2 h;
Step 1.
tert-Butyl [4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetate
1.0M Potassium tert-butoxide in THF (2.4 mL, 2.4 mmol) was added to a solution of 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.39 g, 2.0 mmol) in N,N-dimethylformamide (6.0 mL) at 0° C.
The reaction mixture was stirred at room temperature for 5 min.
After cooled to 0° C., to the mixture was added t-butyl bromoacetate (0.5 mL, 3 mmol).
The reaction was stirred at room temperature for 2 h, then diluted with ethyl acetate, washed with sat. NaHCO3, water, brine, dried over Na2SO4, filtered and concentrated.
The product (0.5 g, 81percent) was purified by chromatography eluting with hexanes/EtOAc (max. EtOAc 30percent). LCMS calculated for C15H26BN2O4 (M+H)+: m/z=309.2. Found: 309.1
77% With potassium carbonate In N,N-dimethyl acetamide at 20℃; for 4 h; Example 2; Synthesis of (+)-2-[4-(2-fluoro-9-hydroxy-9-trifluoromethyl-9H-fluoren-4-yl)-pyrazol-1-yl]-propane-1,3-diol (compound No. 595); Step 1; [4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyrazol-1-yl]-acetic acid t-butyl ester; 4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)-1,3,2-dioxaborolane (10 g), N,N-dimethylacetamide (100 ml), potassium carbonate (17.8 g) and t-butyl bromoacetate (9.9 ml) were mixed, and the mixture was stirred at room temperature for 4 hr. The reaction mixture was filtered through celite. Water and ethyl ether were added to the filtrate, and the mixture was partitioned in a separatory funnel. The aqueous layer was extracted with ethyl ether, and the organic layers were combined. The organic layer was washed 3 times with water and once with saturated brine, dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure, hexane (50 ml) was added to the obtained residue and the mixture was stirred. This slurry was filtered, and the obtained solid was washed with hexane, and dried under reduced pressure to give the title compound (12.23 g, 77percent).1H-NMR (DMSO-D6) δ: 7.92 (1H, d, J=0.7 Hz), 7.59 (1H, d, J=0.5 Hz), 4.95 (2H, s), 1.42 (9H, s), 1.25 (12H, s).
63% With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 8 h; 4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl) -1H-pyrazole (0.5 g, 2.6 mmol) Cesium carbonate (1.3 g, 3.9 mmol) was dissolved in N, N-dimethylformamide (10 mL) Tert-butyl bromoacetate (0.6 mL, 3.9 mmol) was added, and the mixture was stirred at room temperature for 8 hours. After completion of the reaction, the reaction mixture was cooled to room temperature, distilled water (50 mL) was added thereto, and the mixture was extracted with ethyl acetate. The organic layer was washed with distilled water and saturated brine, dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel column chromatography (ethyl acetate: n-hexane = 1: 3) to give the title compound 56-a (1.1 g, 63percent) as a yellow solid.
12.23 g With potassium carbonate In N,N-dimethyl-d6-formamide at 20℃; for 4 h; Step 8
t-Butyl[4-(4,4,5,5-tetramethyl[1,3,2]dioxaborolan-2-yl)-1H-pyrazol-1-yl]acetate
4,4,5,5-Tetramethyl-2-(1H-pyrazol-4-yl)[1,3,2]dioxaborolane (10 g), N,N-dimethylacetamide (100 ml), potassium carbonate (17.8 g) and t-butyl bromoacetate (9.9 mL) were mixed, and the mixture was stirred at room temperature for 4 hr.
The reaction mixture was filtered through celite.
Water and diethylether were added to the filtrate, and the mixture was poured into a separating funnel and partitioned.
The aqueous layer was extracted again with diethyl ether, and combined with the organic layer.
The obtained organic layer was washed three times with water, once with saturated brine, and dried over anhydrous sodium sulfate.
The insoluble material was filtered off, and the filtrate was concentrated under reduced pressure.
To the obtained residue was added hexane (50 ml) and the mixture was slurry washed (suspension stirred).
The suspension was filtered, and the obtained solid was washed with hexane, and dried under reduced pressure to give the title compound (12.23 g).
1H-NMR (400 MHz, DMSO-D6) δ: 7.92 (1H, d, J=0.7 Hz), 7.59 (1H, d, J=0.5 Hz), 4.95 (2H, s), 1.42 (9H, s), 1.25 (12H, s).

Reference: [1] Patent: WO2016/123796, 2016, A1, . Location in patent: Page/Page column 49; 50
[2] Patent: US2008/39457, 2008, A1, . Location in patent: Page/Page column 36
[3] Patent: US2013/59835, 2013, A1, . Location in patent: Paragraph 1146
[4] Patent: US2014/249132, 2014, A1, . Location in patent: Paragraph 0424
[5] Patent: US2010/240634, 2010, A1, . Location in patent: Page/Page column 57-58
[6] Patent: KR101798840, 2017, B1, . Location in patent: Paragraph 1111-1114
[7] Patent: WO2008/64157, 2008, A1, . Location in patent: Page/Page column 87
[8] Patent: WO2010/75270, 2010, A1, . Location in patent: Page/Page column 126-127
[9] Patent: US2014/296316, 2014, A1, . Location in patent: Paragraph 0286; 0287; 0288
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