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CAS No. : | 1000522-43-9 | MDL No. : | MFCD09925072 |
Formula : | C7H6ClNO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | AUCKAGADUXSVKT-UHFFFAOYSA-N |
M.W : | 171.58 | Pubchem ID : | 46737473 |
Synonyms : |
|
Num. heavy atoms : | 11 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.14 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 40.79 |
TPSA : | 50.19 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.65 cm/s |
Log Po/w (iLOGP) : | 1.23 |
Log Po/w (XLOGP3) : | 0.98 |
Log Po/w (WLOGP) : | 1.36 |
Log Po/w (MLOGP) : | 0.66 |
Log Po/w (SILICOS-IT) : | 1.69 |
Consensus Log Po/w : | 1.18 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -1.79 |
Solubility : | 2.76 mg/ml ; 0.0161 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.62 |
Solubility : | 4.1 mg/ml ; 0.0239 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.41 |
Solubility : | 0.661 mg/ml ; 0.00385 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.65 |
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 |
---|---|---|
51% | With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20℃; for 5h; | General procedure: Lithium hydroxide monohydrate (127 mg, 3.03 mmol) in water (0.5 ml_) was added to (3- (trifluoromethyl)-l H-pyrazol-1 -yl)acetic acid ethyl ester (250 mg, 1 .125 mmol) in THF (5 ml_). The mixture was stirred at room temperature for 5 hours then the reaction mixture volume was reduced to one third by evaporation in vacuo. The aqueous residue was acidified using aqueous HCI (2M) to pH5. The resulting off white solid was filtered, collected and dried, washed with ether to afford the title compound as a white solid (42 mg, 19%). 1HNMR (400MHz, DMSO-d6): delta ppm 5.07 (s, 2H), 6.73 (s, 1 H), 7.95 (s, 1 H). LCMS Rt = 2.93 minutes MS m/z 195 [M+H]+ |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Example 46 N-(5-[2-Amino-7-(2-hydroxy-1,1-dimethylethyl)-7H-pyrrolo[2,3-d]pyrimidin-5-yl]carbonyl}pyridin-3-yl)-2-(5-chloropyridin-2-yl)acetamide (5-Chloropyridin-2-yl)acetic acid (26.1 g, 152 mmol) (see Preparation 90) was added to (5-aminopyridin-3-yl){7-(2-[tert-butyl(dimethyl)silyl]oxy}-1,1-dimethylethyl)-2-[(2,4-dimethoxybenzyl)amino]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone (75.0 g, 130 mmol) (see Preparation 51), 1-propylphosphonic acid cyclic anhydride (187 mL, 317 mmol, 50% solution in EtOAc) and triethylamine (61.9 mL, 444 mmol) in THF (423 mL). The mixture was stirred at 25 C. for 2 hours then saturated aqueous sodium bicarbonate (400 mL) was added and the organic layer was separated. The aqueous phase was extracted with EtOAc (400 mL) and all organic phases were combined and dried over sodium sulfate then evaporated in vacuo. The residue brown solid was dissolved in trifluoroacetic acid (300 mL) and the solution was stirred at 50 C. for 3 hours then evaporated in vacuo. Methanol (1800 mL) was added to the residue and the mixture was filtered. The filtrate was evaporated in vacuo and azeotroped with ethanol (3*200 mL). Potassium carbonate (87.7 g, mmol) was added to the crude trifluoroacetamide in methanol (300 mL) and the mixture was stirred at room temperature for 16 hours. The mixture was poured into water (2000 mL) and filtered. The solid was washed with water (200 mL) then triturated with ethanol (2*200 mL at room temperature then 380 mL at 50 C.) to afford the title compound as a yellow solid in 48% yield, 29.9 g. 1H NMR (400 MHz, DMSO-d6) delta: 1.64 (s, 6H), 3.90 (d, 2H), 3.95 (s, 2H), 5.05 (t, 1H), 6.54 (br s, 2H), 7.49 (d, 1H), 7.69 (s, 1H), 7.92 (dd, 1H), 8.40 (m, 1H), 8.56 (m, 1H), 8.64 (d, 1H), 8.94 (d, 1H), 8.96 (s, 1H), 10.71 (s, 1H); LCMS (System 3): Rt=9.92 min; m/z 480 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In tetrahydrofuran; ethyl acetate; at 20℃; for 16h; | 4-Cyclopropyl-[1,2,3]triazol-1-yl)acetic acid (Preparation 121 , 85 mg, 0.508 mmol) and (4-Aminopyridin-2-yl)-(7-tert-butyl-7H-pyrrolo[2,3-d]pyrimidin-5-yl)methanone (Preparation 29, 100 mg, 0.338 mmol) were dissolved in THF (5 mL), followed by the addition of Et3N (0.165 mL, 1 .18 mmol) and 1 -propylphosphonic acid cyclic anhydride (50% solution in EtOAc, 0.507 mL, 0.845 mmol) at room temperature. The resultant mixture was stirred at room temperature for 16 hours and then diluted with ethyl acetate (20 mL). The organic layer was washed with aqueous saturated NaHCO3 solution, water, brine, dried over sodium sulphate and evaporated to dryness in vacuo. The crude residue was purified using preparative TLC eluting with 3% MeOH in DCM to afford the title compound as brown solid in 25% yield, 37 mg. 1H NMR (400 MHz, DMSO-d6): delta ppm 0.72-0.73 (m, 2H), 0.90-0.93 (m, 2H), 1 .82 (s, 9H), 1 .95-1 .98 (m, 1 H), 5.29 (s, 2H), 7.82 (d, 1 H), 7.86 (s, 1 H), 8.23 (s, 1 H), 8.65 (d, 1 H), 8.97 (s, 1 H), 9.20 (s, 1 H), 9.59 (s, 1 H), 1 1 .16 (br, 1 H). LCMS Rt = 3.17 minutes MS m/z 445 [M+H]+. The following examples were prepared according to Method 2 (Example 36) followed by method 1 Step 2 using 4M HCI in dioxan, using (4-aminopyridin-2-yl){7-[(1 R)-1 -methyl- 2-(tetrahydro-2H-pyran-2-yloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone (Preparation 22) or (4-aminopyridin-2-yl){7-[(1 S)-1 -methyl-2-(tetrahydro-2H-pyran-2- yloxy)ethyl]-7H-pyrrolo[2,3-d]pyrimidin-5-yl}methanone (Preparation 23) and the appropriate acetic acids. |
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