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CAS No. : | 916177-00-9 | MDL No. : | MFCD18427599 |
Formula : | C13H14BNO6S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | RCUJDNBFRQOHOY-UHFFFAOYSA-N |
M.W : | 323.13 | Pubchem ID : | 58897027 |
Synonyms : |
|
Num. heavy atoms : | 22 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.15 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 79.57 |
TPSA : | 114.21 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) : | -7.31 cm/s |
Log Po/w (iLOGP) : | 0.0 |
Log Po/w (XLOGP3) : | 1.35 |
Log Po/w (WLOGP) : | 0.58 |
Log Po/w (MLOGP) : | 0.63 |
Log Po/w (SILICOS-IT) : | -1.34 |
Consensus Log Po/w : | 0.24 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.73 |
Solubility : | 0.596 mg/ml ; 0.00185 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.35 |
Solubility : | 0.144 mg/ml ; 0.000446 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.56 |
Solubility : | 0.896 mg/ml ; 0.00277 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.13 |
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: |
* 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 |
---|---|---|
100% | With potassium carbonate;tetrakis(triphenylphosphine) palladium(0); In 1,4-dioxane; water; at 170℃; for 0.166667h;Microwave irradiation; | Example 2; Preparation of PyrroIyl-PyrroIo[2,3-i/]Pyrimidines of the Invention; [ 0238] 4-(7ff-IVr<>K2^^pyrimidin^-yl)-l-(toluene-4-sulfonyl)-lJy- pyrrole-2-carboxylic acid methyl ester (3'); Under N2, Compound 1 ' (1.3 g, 8.49 mmol) and compound T (1.1 equivalent, 9.34 mmol) and K2CO3 (3.3 equivalent, 28 mmol) were dissolved into 9 mL of dioxane and 3 mL of H2O in a microwave. To this reaction mixture, catalytic amount of Pd(PPh3^ was added and the tube was under <n="69"/>microwave irradiation at 1700C for 10 min. After cooled down the reaction mixture, the product crashed out and filtered off the solid, washed with H2O and CH3CN respectively to obtain title compound 3' quantatively. MS +1 = 397.2. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
74.94% | With palladium diacetate; sodium carbonate; tricyclohexylphosphine tetrafluoroborate; In water; at 20 - 85℃;Inert atmosphere; Reflux; Large scale; | In Step 2, a clean and dry 300 L glass-lined reactor was evacuated to -0.08 MPa, and then filled with nitrogen to normal pressure three times. Glycol dimethyl ether (73.10 kg) was charged into the 300 L glass-lined reactor at 20-30C. ASYM-112060 (Asymchem) (10.46 kg) and ASYM-111938 (Asymchem) (12.34 kg, 11.64 kg after corrected) were added into the mixture in turn under the protection of nitrogen. Maintaining the temperature at 20-30C, purified water (10.50 kg) and anhydrous sodium carbonate (5.67 kg) were added into the mixture. Palladium acetate (0.239 kg) and tricyclohexylphosphonium tetrafluoroborate (0.522 kg) were added into the mixture under the protection of nitrogen. After addition, the mixture was evacuated to -0.06 MPa, and then filled with nitrogen to normal pressure. This was repeated for ten times until residual oxygen was 300 ppm. The mixture was heated to 75-85C for refluxing. The mixture reacted at 75-85C. After 4 h, the mixture was sampled and analyzed by HPLC every 2-3 h for content of ASYM83 112060. The content of ASYM-112060 was 6.18%, so additional ASYM-111938 (0.72 kg) was added and continued reaction until the content of ASYM-112060 was 3%. The mixture was cooled to 25-35C and filtered with a 30 L stainless steel vacuum filter. The filter cake was soaked and washed twice with THE (14.10kg). The filtrate and washing liquor were combined and concentrated at 50C under reduced pressure (-0.08 MPa) until 10-15 L remained. The mixture was cooled to 15-25C. Methanol (11.05 kg) was added into the concentrated mixture. Then the mixture was stirred for crystallization. After 2 h, the mixture was sampled and analyzed by HPLC every 2-4 h until the wt% of the mother liquor was 2%. The mixture was filtered with a 30 L stainless steel vacuum filter. The filter cake was soaked and washed twice with methanol (8.30 kg). The filter cake was transferred into a 50 L plastic drum. Then ethyl acetate (7.10 kg) and petroleum ether (46.30 kg) were added into the drum. The mixture was stirred for 1.5-2 h and then filtered with a nutsche filter. The filter cake was soaked and washed with petroleum ether (20.50 kg). The filter cake was dried in the nutsche filter under nitrogen at 30-40C. After 8 h, the solid was sampled and Karl Eischer (KE) analysis was performed in intervals of 4-8 h to monitor the drying process. Drying was completed when the KE result was 1.0% water. During drying, the solid was turned over and mixed every 4-6 h. 12.15 kg of product was recovered as a brownish yellow solid at 98.32% purity. |
74.94% | With palladium diacetate; sodium carbonate; tricyclohexylphosphine tetrafluoroborate; In 1,2-dimethoxyethane; water; at 20 - 85℃; under 760.051 Torr; for 4.0h;Inert atmosphere; Large scale; | In Step 2, a clean and dry 300 L glass-lined reactor was evacuated to <-0.08 MPa, and then filled with nitrogen to normal pressure three times. Glycol dimethyl ether (73.10 kg) was charged into the 300 L glass-lined reactor at 20-30C. ASYM-1 12060 (Asymchem) (10.46 kg) and ASYM-1 1 1938 (Asymchem) (12.34 kg, 1 1 .64 kg after corrected) were added into the mixture in turn under the protection of nitrogen. Maintaining the temperature at 20-30C, purified water (10.50 kg) and anhydrous sodium carbonate (5.67 kg) were added into the mixture. Palladium acetate (0.239 kg) and tricyclohexylphosphonium tetrafluoroborate (0.522 kg) were added into the mixture under the protection of nitrogen. After addition, the mixture was evacuated to?-0.06 MPa, and then filled with nitrogen to normal pressure. This was repeated for ten times until residual oxygen was?300 ppm. The mixture was heated to 75-85C for refluxing. The mixture reacted at 75-85C. After 4 h, the mixture was sampled and analyzed by HPLC every 2-3 h for content of ASYM- 1 12060. The content of ASYM-1 12060 was 6.18%, so additional ASYM-1 1 1938 (0.72 kg) was added and continued reaction until the content of ASYM-1 12060 was ?3%. The mixture was cooled to 25-35C and filtered with a 30 L stainless steel vacuum filter. The filter cake was soaked and washed twice with THF (14.10kg). The filtrate and washing liquor were combined and concentrated at <50C under reduced pressure (<-0.08 MPa) until 10-15 L remained. The mixture was cooled to 15-25C. Methanol (1 1.05 kg) was added into the concentrated mixture. Then the mixture was stirred for crystallization. After 2 h, the mixture was sampled and analyzed by HPLC every 2-4 h until the wt% of the mother liquor was?2%. The mixture was filtered with a 30 L stainless steel vacuum filter. The filter cake was soaked and washed twice with methanol (8.30 kg). The filter cake was transferred into a 50 L plastic drum. Then ethyl acetate (7.10 kg) and petroleum ether (46.30 kg) were added into the drum. The mixture was stirred for 1 .5-2 h and then filtered with a nutsche filter. The filter cake was soaked and washed with petroleum ether (20.50 kg). The filter cake was dried in the nutsche filter under nitrogen at 30-40X. After 8 h, the solid was sampled and Karl Fischer (KF) analysis was performed in intervals of 4-8 h to monitor the drying process. Drying was completed when the KF result was <1.0% water. During drying, the solid was turned over and mixed every 4-6 h. 12.15 kg of product was recovered as a brownish yellow solid at 98.32% purity. |
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