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CAS No. : | 118062-05-8 | MDL No. : | MFCD01318183 |
Formula : | C9H13BO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LDQLSQRFSNMANA-UHFFFAOYSA-N |
M.W : | 212.01 | Pubchem ID : | 2773582 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 55.74 |
TPSA : | 68.15 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.07 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 0.74 |
Log Po/w (WLOGP) : | -0.61 |
Log Po/w (MLOGP) : | -0.5 |
Log Po/w (SILICOS-IT) : | -0.69 |
Consensus Log Po/w : | -0.21 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.65 |
Solubility : | 4.72 mg/ml ; 0.0223 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.75 |
Solubility : | 3.77 mg/ml ; 0.0178 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.68 |
Solubility : | 4.44 mg/ml ; 0.0209 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.57 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In ethanol; water; toluene; at 100℃; | (The following reaction is done in an N2 atmosphere.) To a solution of <strong>[118062-05-8]2,3,4-Trimethoxyphenylboronic acid</strong> (32) (1.40g, 6.60mmol) in toluene (15.0mL) is added EtOH (2.0mL), Pd(PPh3)4 (208mg, 0.18mmol) and Na2CO3·10H2O (4.81g, 16.80mmol) in water (5.2mL). The resulting mixture is carefully degassed (5 times alternating vacuum and flushing with N2). A solution of Methyl-3-bromobenzoate (9) (1.29g, 6.00mmol) in toluene (9.0mL) is added by syringe, the resulting mixture is again carefully degassed and stirred overnight at 100C. Partition the mixture between brine/EtOAc (1+1), separate layers, extract the aqu. layer with EtOAc (3x), wash the combined organic layer with brine, dry with Na2SO4 and remove solvent. Purify crude product by preparative radial chromatography (silica gel, EtOAc/CyH 1+5) to obtain 2',3',4'-Trimethoxy-biphenyl-3-carboxylic acid methyl ester (33) as a yellowish oil (1.07g, 58%). 1H NMR (400MHz, CDCl3): 3.66 (s, 3 H); 3.89 (s, 3 H); 3.92 (s, 6 H); 6.74 (d, 1 H, J= 8.6Hz); 7.03 (d, 1 H, J = 8.6Hz); 7.44 (t, 1 H, J = 7.8Hz); 7.70 (d, 1 H, J = 7.6Hz); 7.97 (d, 1 H, J = 7.8Hz); 8.15 (br.s 1 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
86% | With tetrakis(triphenylphosphine) palladium(0); potassium phosphate monohydrate; In 1,2-dimethoxyethane; at 150℃; for 1.5h;Microwave irradiation; | General procedure: To degassed solutions of 1 equiv of substituted 2-bromo-benzaldehydes 10, 13 or 14 in DME were added 1.5 equiv of boronic species, 3 equiv of K3PO4·H2O and 0.05 equiv of Pd(PPh3)4; the suspensions were heated under microwave irradiation (6 bars, 80-150 watts) for 1 h 30 min at 150 C. The resulting mixtures were filtered (washed with Et2O or EtOAc) and concentrated under reduced pressure. The crude products were then purified by flash chromatography. |
With tetrakis(triphenylphosphine) palladium(0); potassium carbonate; lithium chloride; In 1,2-dimethoxyethane; water; | Preparation of the cyclization precursor is directly analogous to that described with reference to Figure 2 inachieving compound 7a/Formula 1. As shown in Figure 3, in accordance with Scheme 3, biaryl 8 is obtained by Suzuki-Miyaura coupling and which has been made previously, is similarly subjected to reaction with vinylmagnesium bromide.The resultant alcohol (9) is then oxidized to ketone 10 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | With tetrakis(triphenylphosphine) palladium(0); potassium phosphate monohydrate; In 1,2-dimethoxyethane; at 150℃; for 1.5h;Microwave irradiation; | General procedure: To degassed solutions of 1 equiv of substituted 2-bromo-benzaldehydes 10, 13 or 14 in DME were added 1.5 equiv of boronic species, 3 equiv of K3PO4·H2O and 0.05 equiv of Pd(PPh3)4; the suspensions were heated under microwave irradiation (6 bars, 80-150 watts) for 1 h 30 min at 150 C. The resulting mixtures were filtered (washed with Et2O or EtOAc) and concentrated under reduced pressure. The crude products were then purified by flash chromatography. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | To a solution of [2-THIOMETHYL-4-CHLOROPYRIMIDINE] [(0. 3410] g, 2.12 mmol) in 1,4-dioxane (21 mL) was added 2,3, 4-trimethoxyphenylboronic acid (0.4950 g, 2.33 mmol) and aq. [NA2C03] (2.3 mL, 2. 0M in water, 4.60 mmol). The mixture was sparged with dry nitrogen gas for 5 min, and then Pd [(PH3P)] [4] (123 mg, 0.106 mmol) was added. The mixture was protected from light and heated at [110C] for 16 h. The mixture was then cooled to room temperature, filtered, concentrated [IN VACUO,] and purified by flash chromatography using EtOAc-hexanes (1: 4) as eluent, to give 0.5920 g of [2-THIOMETHYL-4- (2,] 3,4-trimethoxyphenyl) pyrimidine (95%) as a yellow solid. To a solution of [2-THIOMETHYL-4- (2,] 3,4-trimethoxyphenyl) pyrimidine (0.5920 g, 2.02 mmol) in [CH2C12] (10 [ML)] was added m-chloroperbenzoic acid (1.05 g, 6.08 mmol), and the solution was stirred for 3 h at which time it was observed to be a white suspension. The suspension was concentrated [IN VACUO,] and [MEOH] (10 mL) was added followed by hydrazine monohydrate (2 mL, 41.2 mmol). The resulting solution was stirred for 16 h and then concentrated to about one-half volume in vacuo. The mixture was allowed to stand for 1 h, and the resulting solid was collected by vacuum filtration and was washed with water. Drying in vacuo afforded 0.3330 g of the title compound (60%) as a light brown solid. MH+ 277. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With cesium fluoride; johnphos;palladium diacetate; In tetrahydrofuran; for 5h;Heating / reflux; | (10-4) Preparation of 2-acetamide-1, 3-BISACETOXY-2- [2- (2 , 3', 4'-trimethoxybiphenyl-4- yl) ethyl] propane A mixture of 2-acetamido-1, 3-BISACETOXY-2- [2- (4-BROMOPHENYL) ETHYL] propane (400 mg), 2,3, 4-TRIMETHOXYPHENYLBORONIC acid (318 mg), palladium acetate (11 mg), di- tert-butyl biphenylphosphine (30 mg), and cesium fluoride (456 mg) in tetrahydrofuran (6 ml) was heated under reflux for 5 hours. Brine was added to the reaction mixture, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over sodium sulfate and concentrated in vacuo. Purification by silica-gel column chromatography using HEXANE/ETHYL acetate 1: 3 gave the title compound (383 mg) as a pale yellow amorphous. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
EXAMPLE 24 1,4-Bis[5-(2,3,4-trimethoxyphenyl)-2-pyridyl]hexahydro-1,4-diazepine Following the procedure of Example 1, an oil was obtained from 1,4-bis(5-bromo-2-pyridyl)hexahydro-1,4-diazepine (115.0 mg, 0.280 mmol) synthesised in Reference Example 1 and <strong>[118062-05-8]2,3,4-trimethoxyphenylboronic acid</strong> (130.0 mg, 0.620 mmol) synthesised from 2,3,4-trimethoxybromobenzne (J. Org. Chem., 23, 16-17 (1958)) in a similar manner as in Reference Example 2. Chloroform-hexane was added to the oil, and the resulting precipitate was collected by filtration to yield the title compound as a yellow crystalline powder (melting point: 192.0-194.0 C.) (57.0 mg, yield: 35%). 1H-NMR (CDCl3) delta: 2.17 (tt, J=6.1, 6.1 Hz, 2 H), 3.65 (dd, J=6.1, 6.1 Hz, 4 H), 3.72 (s, 6 H), 3.89 (s, 6 H), 3.92 (s, 6 H), 3.96 (s, 4 H), 6.60 (d, J=8.8 Hz, 2 H), 6.73 (d, J=8.5 Hz, 2 H), 7.00 (d, J=8.5 Hz, 2 H), 7.67 (dd, J=2.4, 8.8 Hz, 2 H), 8.28 (d, J=2.4 Hz, 2 H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92.1% | EXAMPLE 35 4-amino-N-propyl-8-(2,3,4-trimethoxyphenyl)-cinnoline-3-carboxamide Using method A, 4-amino-8-bromo-N-propyl-cinnoline-3-carboxamide (106 mg, 0.34 mmol) and <strong>[118062-05-8]2,3,4-trimethoxyphenyl boronic acid</strong> (206 mg, 0.97 mmol) were reacted to afford the title compound (124 mg, 92.1% yield) as a pale-yellow solid. 1H NMR (300 MHz, CDCl3) delta 8.56 (br, 1H), 7.88 (dd, J=8.2 Hz, J'=1.5 Hz, 1H), 7.76 d, J=6.3 Hz, 1H), 7.69 (t, J=7.6 Hz, 1H), 7.09 (d, J=8.6 Hz, 1H), 6.80 (d, J=8.6 Hz, 1H), 3.94 (s, 3H), 3.92 (s, 3H), 3.62 (s, 3H), 3.45 (q, J=6.7 Hz, 2H), 1.65 (m, J=7.2 Hz, 2H), 0.99 (t, J=7.4 Hz, 3H) MS APCI, m/z=397 (M+H) HPLC 1.70 min. |
Tags: 118062-05-8 synthesis path| 118062-05-8 SDS| 118062-05-8 COA| 118062-05-8 purity| 118062-05-8 application| 118062-05-8 NMR| 118062-05-8 COA| 118062-05-8 structure
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