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CAS No. : | 1439399-58-2 | MDL No. : | MFCD28167826 |
Formula : | C26H24F3N7O3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PRAAPINBUWJLGA-UHFFFAOYSA-N |
M.W : | 571.57 | Pubchem ID : | 71577426 |
Synonyms : |
CB-839;GLS1 Inhibitor III
|
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 |
---|---|---|
76% | With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide In N,N-dimethyl acetamide; ethyl acetate at 20.1 - 26.1℃; for 4 h; | To a solution of 110826 (5.5 g, 12.3 mmol, 1.0 equiv.) in N,N-dimethylacetamide (44 mL,8.0 vol. versus 110826) in a 250 mL three neck round-bottom flask was added 2-pyridylacetic acid (2.56 g, 14.8 mmol, 1.2 equiv.). Propylphosphonic anhydride (11.0 g of50percent solution in ethyl acetate, 17.3 mmol, 1.41 equiv.) was charged into a 25 mL additionfunnel and added dropwise to reaction solution at a rate of 5mL/min. During the additionthe internal temperature increased from 20.1°C to 26.1°C. The reaction usually goes tocompletion after 4 hours (determined by LC/MS). Reaction solution was then cooled a 0°Cbath and diluted with methyl ethyl ketone (50 mL). To the stirred reaction solution is added H20 (50 mL). The pH was adjusted to pH6 with 2.5N sodium hydroxide(aq) (28 mL). The yellow precipitate was collected by suction filtration and rinsed with isopropyl alcohol and water (1:1, 50 mL). The air dried solid was then transferred to a 100 mL round bottomflask and slurried in isopropyl alcohol and water (9:1, 50 mL). The slurry was heated to an internal temperature of 65.1°C for 8 hours and cooled to ambient temperature over 16 hours. The off-white precipitate was collected by suction filtration and rinsed 1 x isopropyl alcohol (1 OmL). The retentate was dried under high vacuum to a constant weight to afford 2-(pyridin-2-yl)-N-(5 -(4-(6-(2-(3 -(trifluoromethoxy)phenyl)acetamido)pyridazin-3 -yl)butyl)-1,3,4-thiadiazol-2-yl)acetamide (CB-839); yield of 5.27 g (76percent). ‘H NMR (300MHz, DMSO-d6) ö 12.67 (s, 1H), 11.32 (s, 1H), 8.53-8.49 (m, 1H), 8.22-8.19 (d, J 9.12Hz, 1H), 7.78-7.76 (t, 1H), 7.58-7.26 (m, 7H), 4.01 (s, 2H), 3.87 (s, 2H), 3.01 (bs, 2H), 2.90(bs, 2H), 1.73 (bs, 4H).The XRD pattern of CB-839 crystalline freebase, Form B is shown in FIG. 6.CB-839 freebase, Form B has 20 values 3.64; 7.32; 7.92; 8.53; 9.30; 9.38; 11.02; 11.98;14.70; 15.54; 15.87; 16.50; 16.59; 18.06; 18.39; 19.10; 20.06; 20.12; 20.61; 21.37; 21.89;22.41; 22.74; 23.72; 24.10; 24.65; 25.14; 25.78; 26.49; 27.32; 27.55; 28.26; 29.88; 31.20;31.80; 31.52; 32.80; 34.30; 35.20; 36.41; 38.53; 40.08; 40.94; and 43.86. |