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CAS No. : | 936091-14-4 | MDL No. : | MFCD15528085 |
Formula : | C26H35N7O2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | JVDOKQYTTYUYDV-UHFFFAOYSA-N |
M.W : | 509.67 | Pubchem ID : | 16722832 |
Synonyms : |
|
Num. heavy atoms : | 36 |
Num. arom. heavy atoms : | 18 |
Fraction Csp3 : | 0.38 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 152.7 |
TPSA : | 110.87 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.43 cm/s |
Log Po/w (iLOGP) : | 3.87 |
Log Po/w (XLOGP3) : | 4.2 |
Log Po/w (WLOGP) : | 4.42 |
Log Po/w (MLOGP) : | 2.27 |
Log Po/w (SILICOS-IT) : | 1.83 |
Consensus Log Po/w : | 3.32 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -5.49 |
Solubility : | 0.00166 mg/ml ; 0.00000325 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -6.24 |
Solubility : | 0.000295 mg/ml ; 0.000000578 mol/l |
Class : | Poorly soluble |
Log S (SILICOS-IT) : | -8.34 |
Solubility : | 0.00000231 mg/ml ; 0.0000000045 mol/l |
Class : | Poorly soluble |
PAINS : | 1.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 3.0 |
Synthetic accessibility : | 4.25 |
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 |
---|---|---|
59% | With caesium carbonate;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In 1,4-dioxane; at 1650℃; for 0.333333h;Microwave irradiation; | [0176] A suspension of intermediate 32 (0.30 g, 1.0 mmol), 3-bromo-iV-tert-butyl- benzenesulfonamide (0.35 g, 1.2 mmol), Pd2(dba)3 (60 mg, 0.066 mmol), Xantphos (70 nig, 0.12 mmol) and cesium carbonate (0.70 g, 2.1 mmol) in dioxane/DMF (3/1, 8 mL) was sealed in a microwave reaction tube and irradiated with microwave at 160 "C for 20 min. After cooling to room temperature, the cap was removed and the resulting mixture filtered and the filtered solid washed with DCM. The filtrate was concentrated and the residue purified by HPLC. The fractions were combined and poured into saturated NaHCO3 solution (40 mL). The combined aqueous layers were extracted with EtOAc (2 x 30 mL) and the combined organic layers washed with brine, dried over anhydrous Na2SO4 and filtered. The filtrate was concentrated and the residue triturated in a mixture of EtOAc/hexanes (1/7, 40 mL). After filtration, the title compound was obtained as an off white solid (0.30 g, 59percent).[0177] 1H NMR (500 MHz, DMSO-d6): delta 1.12 (s, 9H), 2.11 (s, 3H), 2.22 (s, 3H), 2.45 (t, J= 4.7 Hz, 4H), 3.02 (t, J- 4.8 Hz, 4H), 6.81 (d, J= 9.1 Hz, 2H), 7.45-7.52 (m, 4H), 7.56 (s, IH), 7.89 (s, IH), 8.10-8.16 (m, 2H), 8.51 (s, IH), 8.70 (s, IH) MS (ES+): m/z 510 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With sodium hydroxide In water for 0.05h; | 10 (N-tert-butyl-3-(5-methyl-2-4-(4-methyl-pyridine) benzenesulfonamide) To a solution of 1.0 g (1.76 g) of 1 tert-butyl-3- (5-methyl-2- [4- (4-methyl- 4-aminopyrimidine) -benzenesulfonamide acetate (III-c) was dissolved in 3 mL of water, and a 1 mL of 4% aqueous solution of sodium hydroxide was added dropwise with stirring. The filter cake was washed with 1 mL deionized water and heated to 50 ° C in vacuo for 6 hours to yield 808 mg of the free compound product (Formula I) in 90% yield. [0094] The iH-NMR spectrum is exactly the same as that reported in U.S. Patent No. W02007 / 053452A1. 1H-NMR (400 MHz, DMS0-d6): S8.70 (s, 1H), 8.51 (s, 1H), 8.16-8.10 (m, 2H), 7.89 (s, 1H) 2H, 3.02 (t, J = 4.8Hz, 4H), 2.45 (d, J = 9.2Hz, 2H), 3.50-7.46 (m, 4H) (T, J = 4.8Hz, 4H), 2.22 (s, 3H), 2.11 (s, 3H), 1.12 (s, 9H) LC-MS (214 nm): m / z 510.1 (M ++ 1); Retention time: 1.570 min; Purity (254 nm): 98.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
92% | With ammonium hydroxide | 8 (Preparation of TG101209): (N-tert-butyl-3-(5-methyl-2-[4-(4-methyl-1-piperazine)anilino]-4-aminopyrimidine A mixture of 1.0 g of N-t-butyl-3- (5-methyl-2- [4- (4-methyl- 1 -piperazine) anilino] (III-a) was dissolved in 3 mL of water (to form a clear solution); and 25% ammonia 7K was slowly added dropwise with stirring to adjust pH = 7.0 to 8.0. A black solid precipitated, which was filtered and dried to give the free compound product, 800 mg, 92% [0084] The iH-NMR spectrum is exactly the same as that reported in U.S. Patent No. W02007 / 053452A1. 1H-NMR (400 MHz, DMS0-d6): S8.70 (s, 1H), 8.51 (s, 1H), 8.16-8.10 (m, 2H), 7.89 (s, 1H) 2H, 3.02 (t, J = 4.8Hz, 4H), 2.45 (d, J = 9.2Hz, 2H), 3.50-7.46 (m, 4H) (T, J = 4.8Hz, 4H), 2.22 (s, 3H), 2.11 (s, 3H), 1.12 (s, 9H) LC-MS (214 nm): m / z 510.1 (M ++ 1); Retention time: 1.570 min; Purity (254 nm): 98.8%. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: dichloromethane 2: N,N-dimethyl-formamide / 6 h / 85 °C 3: triethylamine / dichloromethane / 3 h | ||
Multi-step reaction with 3 steps 1: hydrogenchloride / methanol; water 2: isopropyl alcohol / 0.5 h / 85 °C 3: ammonium hydroxide / pH 7 - 8 | ||
Multi-step reaction with 3 steps 1: 0.5 h 2: isopropyl alcohol / 6 h / 85 °C 3: sodium hydroxide / water / 0.05 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: isopropyl alcohol / 6 h / 85 °C 2: sodium hydroxide / water / 0.05 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: N,N-dimethyl-formamide / 6 h / 85 °C 2: triethylamine / dichloromethane / 3 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
97% | With triethylamine In dichloromethane for 3h; | 9 N-tert-Butyl-3- (5-methyl-2- [4- (4- methyl- 1 -piperazine) anilino] Sulfonamide To a solution of 1.0 g (1.60 g) of 1 tert-butyl-3- (5-methyl-2- [4- (4-methyl- Yl] -4-aminopyrimidine) benzenesulfonamide trifluoroacetate (III-b) was mixed with 10 mL of methylene chloride, and the mixture was stirred dropwise Triethylamine; the resulting suspension was stirred for an additional 3 hours. The solvent was evaporated under reduced pressure and excess triethylamine was added; 3 mL of water was added to the residue and stirring was continued for 5 minutes; the suspended black solid was the product, triethylamine hydrochloride was dissolved in water; the suspension was filtered, dried , To give 790 mg of the free compound product (Formula I) in 97% yield. [0089] The iH-NMR spectrum is exactly the same as that reported in U.S. Patent No. W02007 / 053452A1. 1H-NMR (400 MHz, DMS0-d6): S8.70 (s, 1H), 8.51 (s, 1H), 8.16-8.10 (m, 2H), 7.89 (s, 1H) 2H, 3.02 (t, J = 4.8Hz, 4H), 2.45 (d, J = 9.2Hz, 2H), 3.50-7.46 (m, 4H) (T, J = 4.8Hz, 4H), 2.22 (s, 3H), 2.11 (s, 3H), 1.12 (s, 9H) LC-MS (214 nm): m / z 510.1 (M ++ 1); Retention time: 1.570 min; Purity (254 nm): 98.8%. |