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CAS No. : | 863127-77-9 | MDL No. : | MFCD08704581 |
Formula : | C22H28ClN7O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | XHXFZZNHDVTMLI-UHFFFAOYSA-N |
M.W : | 506.02 | Pubchem ID : | 11540687 |
Synonyms : |
BMS-354825 monohydrate
|
Chemical Name : | N-(2-Chloro-6-methylphenyl)-2-((6-(4-(2-hydroxyethyl)piperazin-1-yl)-2-methylpyrimidin-4-yl)amino)thiazole-5-carboxamide hydrate |
Num. heavy atoms : | 34 |
Num. arom. heavy atoms : | 17 |
Fraction Csp3 : | 0.36 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 7.0 |
Num. H-bond donors : | 4.0 |
Molar Refractivity : | 141.68 |
TPSA : | 143.98 Ų |
GI absorption : | Low |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | Yes |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -7.18 cm/s |
Log Po/w (iLOGP) : | 3.37 |
Log Po/w (XLOGP3) : | 3.11 |
Log Po/w (WLOGP) : | 2.3 |
Log Po/w (MLOGP) : | 0.58 |
Log Po/w (SILICOS-IT) : | 3.33 |
Consensus Log Po/w : | 2.54 |
Lipinski : | 1.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 1.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -4.78 |
Solubility : | 0.00842 mg/ml ; 0.0000166 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.8 |
Solubility : | 0.000798 mg/ml ; 0.00000158 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -6.88 |
Solubility : | 0.000067 mg/ml ; 0.000000132 mol/l |
Class : | Poorly soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 3.94 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
83.2% | Stage #1: With N-ethyl-N,N-diisopropylamine In butan-1-ol at 118℃; for 4.5 h; Stage #2: With water In ethanol |
To a mixture of compound 5D (4.00 g, 10.14 mmol) and hydroxyethylpiperazine (6.60 g, 50.69 mmol) in n-butanol (40 mL) was added DIPEA (3.53 mL, 20.26 mmol). The slurry was heated at 118°C for 4.5h, then cooled slowly to room temperature. The solid was collected by vacuum filtration, washed with n- butanol (5 mL), and dried. The product (5.11 g) was dissolved in hot 80percent EtOH-H2O (80 mL), and the solution was clarified by filtration. The hot solution was slowly diluted with water (15 mL) and cooled slowly to room temperature. The solid was collected by vacuum filtration, washed with 50percent ethanol-water (5 mL) and dried affording 4.27 g (83.2 percent yield) of N- (2-chloro-6-methylphenyl)-2- (6- (4- (3- hydroxyethyl) piperazin-1-yl)-2-methylpyrimidin-4-ylamino) thiazole-5-carboxamide as monohydrate. 1H NMR (400 MHz, DMSO-d6) # 2.23 (s, 3H), 2.40 (s, 3H), 2.42 (t, 2H, J=6), 2.48 (t, 4H, J=6.3), 3.50 (m, 4H), 3.53 (q, 2H, J=6), 4.45 (t, 1H, J=5.3), 6.04 (s, 1H), 7.25 (t, 1H, J=7.6), 7.27 (dd, 1H, J=7.6, 1.7), 7.40 (dd, 1H, J=7.6, 1.7), 8.21 (s, 1H), 9. 87 (s, 1H), 11.47. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
21 g | With water In methanolHeating | Take 25g of dasatinib into 2000ml of methanol, stir and heat to dissolve, filter it while hot, add 500ml of water under stirring in the filtrate, stop stirring, naturally cool, slowly precipitate fine crystals, leave at room temperature overnight, and then add 1500ml of water After the addition, continue to crystallize for 10 hours.The precipitated white crystals were filtered off with suction, washed with a small amount of methanol, vacuum-dried at 60° C., and phosphorus pentoxide was used for drying to obtain 21 g of a white crystalline solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With caesium carbonate; potassium iodide In acetonitrile for 6 h; Reflux | 2-bromoethanol (3.9 g, 0.03), Cs2CO3 (10.2 g, 0.03 mol), KI (0.17g, 1 mmol) was added to a stirred suspension of compound 2 (7.0 g, 0.02 mol), in acetonitrile (105.0 mL) and refluxed for 6h. Water (280.0 mL) was added slowlyat 75-80°C, cooled to 25-30°C and stirred for 2h. The precipitated solid was collected by vacuum filtration, washed the wet cake with Acetonitrile (28.0 mL), water (35.0 mL), yielded the final compound, Dasatinib monohydrate 1 (7.4 g, 93percent) as a white solid. MR: 279-280 °C (free base); IR (KBr, cm-1): 3421.5 (N-H), 3250.58 (O-H), 1618.3 (C=O); UV (Methanol): max,322.16 nm; 1H NMR spectrum (400 MHz, DMSO-d6), δ, ppm (J, Hz): 10.47 (bs, 1H, thiazole-NH), 9.88 (s, 1H,amide-NH), 8.22 (s, 1H, thiazole-H), 7.40 (dd, 1H, J =6.1, 1.2, Ar-H), 7.30-7.23 (m, 2H, J =7.3, Ar-H), 6.04 (s,1H, pyrimidine-H), 4.46 (t, J = 4.8, -OH), 3.54-3.51 (m, 6H, -CH2CH2OH & piperazine-CH2), 2.48-2.46 (m, 4H,piperazine-CH2), 2.44-2.42 (m, 2H, -CH2CH2OH), 2.40 (s, 3H, Ar-CH3), 2.24 (s, 3H, pyrimidine-CH3); 13C NMRspectrum (100 MHz, DMSO-d6), δ, ppm: 165.2 (pyrimidine-C), 162.6 (pyrimidine-C), 162.4 (pyrimidine-C),160.0 (amide-C), 156.9 (thiazole-C), 140.9 (Ar-C), 138.8 (thiazole-C), 133.5 (thiazole-C), 132.5 (Ar-C), 129.0(Ar-C), 128.2 (Ar-C), 127.0 (Ar-C), 125.7 (pyrimidine-C), 82.6 (pyrimidine-C), 60.2 (piperazine-2C), 58.5(piperazine-2C), 52.7 (CH2), 43.6 (CH2), 25.6 (Ar-CH3), 18.4 (pyrimidine-CH3); MS (ESI) m/z 488.6 [M + H] +;Anal. Calcd percent for C22H28ClN7O3S: C 54.15; H 5.37; N 20.09. Found: C 54.13; H 5.36; N 20.13; HPLC Purity:99.91percent (tR = 27.4 min.); 2-brpmoethanol content by Headspace GC: 3 ppm; p-XRD: Observed 2 values at 18.0,18.4, 19.2, 19.6, 21.2, 24.5, 25.9; 28.0; DSC (Differential scanning calorimetry): Obtained endotherm at 287.23°C(92.05 J/g); TGA (Thermogravimetric analysis): weight (water) loss (percent) = 3.488 [5,9]. |