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CAS No. : | 146140-95-6 | MDL No. : | MFCD01114645 |
Formula : | C11H16BNO3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | MXRAJVMTCAUABO-UHFFFAOYSA-N |
M.W : | 221.06 | Pubchem ID : | 4193502 |
Synonyms : |
|
Num. heavy atoms : | 16 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 4 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 64.74 |
TPSA : | 69.56 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) : | -6.26 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.96 |
Log Po/w (WLOGP) : | 0.16 |
Log Po/w (MLOGP) : | 0.71 |
Log Po/w (SILICOS-IT) : | -0.43 |
Consensus Log Po/w : | 0.48 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.46 |
Solubility : | 0.768 mg/ml ; 0.00348 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.05 |
Solubility : | 0.199 mg/ml ; 0.0009 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.51 |
Solubility : | 0.689 mg/ml ; 0.00312 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.94 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H319 | 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 |
---|---|---|
76% | With potassium carbonate In ethanol; toluene for 72h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With sodium carbonate In 1,2-dimethoxyethane; water for 7h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1: 38% 2: 18% | With sodium carbonate In 1,2-dimethoxyethane; water for 12h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | Preparation of N-(2-Pyrimidin-2-yl)phenyl)pivalamide (3d): To a 500L glass-lined reactor, under N2, was added glycol dimethyl ether (152.3 kg, 5L/kg). Then <strong>[1722-12-9]2-chloropyrimidine</strong> (18.4 kg, 160 moles, 1.01 equiv.) was added with stirring, followed by Pd[(Pli3)P]4 (3.65 kg, 3.2 moles, 0.02 equiv.). The resulting mixture was stirred at0 15-25 0C for 20-30 min and then N-(2,2-dimethyl-l-propinamide)l -phenyl -boronic acid (3c) (35 Kg of product, containing additional 11 kg of salts, 158 moles, 1.0 equiv.) was <n="61"/>added in one portion. After addition, aqueous Na2CO3 solution (132.8 kg, 2 M) was added quickly and the mixture heated to 78-83 0C and refluxed for 3h. The reaction was monitored by HPLC using method H until SM (3c) was < 3 %. The mixture was then slightly cooled to 70-75 0C, quenched by addition of cold purified water (5-10 0C, 525 kg) and stirring continued at 0-10 0C for 1-2 h. The mixture was then filtered by centrifuge and the cake washed with purified water. The wet product from 4 batches (7, 35, and 35 kg scale) was combined and dried on a tray dryer for a week and then on a rotary conical dryer but some water (at least 3 % weight) could not be removed. The title compound (3d) was obtained as a yellow wet solid (157 kg, > 100 %, purity > 98 % determined by method F). Typical retention time for product was 15.9 min. | |
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; water; at 20 - 83℃; | A 5 L flask was charged with the above depicted boronic acid as a tetrahydrate (281.4 grams, 960 mmoles), <strong>[1722-12-9]2-chloropyrimidine</strong> (100 g, 874 mmoles), NaHCO3 (146.8 grams, 1.746 moles), and Pd(PPh3)4 (10.0 grams, 8.72 mmoles). Water (1 L) and dimethoxyethane (1 L) were added, and the mixture was heated slowly to 83 C. (internal temperature) over a 1 hour period with overhead stirring. After ~2 hours all solids had dissolved. The reaction was allowed to stir for 8 hours. The mixture was cooled to room temperature and stirred overnight after which time a thick precipitate had formed. The crude mixture was diluted with water (2 L) and stirred for an additional 2 hours after which time the mixture was filtered and the solids were washed sequentially with water, 0.1 N NaOH, and water again. The solids were then dried under high vacuum at 50 C. to afford the title compound (~233 grams) as a tan powder. | |
With sodium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 0 - 83℃; for 4.33333 - 5.5h;Heating / reflux; | In a 500 L glass-lined reactor, under N2, was added glycol dimethyl ether (152.3 Kg, 5L/Kg). Then <strong>[1722-12-9]2-chloropyrimidine</strong> (18.4 Kg, 160 moles, 1.01 equiv.) was added with stirring, followed by Pd[(Ph3)P]4 (3.65 Kg, 3.2 moles, 0.02 equiv.). The resulting mixture was stirred at 15-25 0C for 20-30 min and then N-(2,2-dimethyl-l-propinamide)l-phenyl- boronic acid (3c) (35 Kg of product, containing additional 11 Kg of salts, 158 moles, 1.0 equiv.) was added in one portion. After addition, aqueous Na2CO3 solution (132.8 Kg, 2 M) was added quickly and the mixture heated to 78-83 0C and refluxed for 3h. The reaction was monitored by HPLC using method H until SM (3c) was < 3 %. The mixture was then slightly cooled to 70-75 0C, quenched by addition of cold purified water (5-10 0C, 525 Kg) and stirring continued at 0-10 0C for 1-2 h. The mixture was then filtered by centrifuge and the cake washed with purified water. The wet product from 4 batches (7, 35, and 35 Kg scale) was combined and dried on a tray dryer for a week and then on a rotary conical dryer but some water (at least 3 % weight) could not be removed. The title compound (3d) was obtained as a yellow wet solid (157 Kg, > 100 %, purity > 98 % determined by method F). Typical retention time for product was 15.9 min. |
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 83℃; for 11h; | Example 1; Pd(PPh3VNaHCO3DME/H,O/reflux [00203] 2,2-Dimethyl-N-(2-pyrimidin-2-yI-phenyI)-propionamide: A 5 L flask was charged with the above depicted boronic acid as a tetrahydrate (281.4 grams, 960 mmoles), 2- chloropyrimidine (100 g, 874 mmoles), NaHCO3 (146.8 grams, 1.746 moles), and Pd(PPh3)4 (10.0 grams, 8.72 mmoles). Water (IL) and dimethoxyethane (IL) were added, and the mixture was heated slowly to 83 0C (internal temperature) over a 1 hour period with overhead stirring. After ~2 hours all solids had dissolved. The reaction was allowed to stir for 8 hours. The mixture was cooled to room temperature and stirred overnight after which time a thick precipitate had formed. The crude mixture was diluted with water (2L) and stirred for an additional 2 hours after which time the mixture was filtered and the solids were washed sequentially with water, 0.1 N NaOH, and water again. The solids were then dried under high vacuum at 50 0C to afford the title compound (-233 grams) as a tan powder. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 20 - 83℃; | A 3 L flask was charged with the above depicted boronic acid as a tetrahydrate (92.1 grams, 314 mmoles), <strong>[17282-04-1]chlorofluoropyridine</strong> (37.6 g, 286 mmoles), NaHCO3 (48.0 grams, 572 mmoles), and Pd(PPh3)4 (3.3 grams, 2.86 mmoles). Water (300 mL) and dimethoxyethane (300 mL) were added, and the mixture was heated slowly to 83 C. (internal temperature) over a 1 hour period with overhead stirring. After ~2 hours all solids had dissolved. The reaction was allowed to stir for 10 hours. The mixture was cooled to room temperature and stirred overnight after which time a thick gum had formed. The crude mixture was diluted with water (2 L) and stirred for an additional 2 hours. The mixture was then allowed to rest without stirring until the gum had settled to the bottom of the flask. The liquid phase was removed via vacuum, then replaced with 0.1 N NaOH and stirred for 15 minutes. The gum was allowed to settle and the liquid removed via vacuum. The gum was then similarly washed three times with water, then transferred to a 1 neck flask as an acetone solution. The mixture was concentrated in vacuo and azeotroped five times with ethyl acetate. | |
With sodium hydrogencarbonate;tetrakis(triphenylphosphine) palladium(0); In 1,2-dimethoxyethane; water; at 83℃; for 13h; | Example 6; [00208] N-[2-(3-Fluoro-pyridin-2-yl)-phenyl]-2,2-diniethyl-propionaniide:; A 3 L flask was charged with the above depicted boronic acid as a tetrahydrate (92.1 grams, 314 mmoles), <strong>[17282-04-1]chlorofluoropyridine</strong> (37.6 g, 286 mmoles), NaHCO3 (48.0 grains, 572 mmoles), and Pd(PPh;,)-. (3.3 grams, 2.86 mmoles). Water (300 mL) and dimethoxyethane (300 mL) were added, and the mixture was heated slowly to 83 C (internal temperature) over a 1 hour period with overhead stirring. After ~2 hours all solids had dissolved. The reaction was allowed to stir for 10 hours. The mixture was cooled to room temperature and stirred overnight after which time a thick gum had formed. The crude mixture was diluted with <n="77"/>water (2L) and stirred for an additional 2 hours. The mixture was then allowed to rest without stirring until the gum had settled to the bottom of the flask. The liquid phase was removed via vacuum, then replaced with 0.1 N NaOH and stirred for 15 minutes. The gum was allowed to settle and the liquid removed via vacuum. The gum was then similarly washed three times with water, then transferred to a 1 neck flask as an acetone solution. The mixture was concentrated in vacuo and azeotroped five times with ethyl acetate. |