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CAS No. : | 1129-35-7 | MDL No. : | MFCD00001823 |
Formula : | C9H7NO2 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KKZMIDYKRKGJHG-UHFFFAOYSA-N |
M.W : | 161.16 | Pubchem ID : | 70791 |
Synonyms : |
|
Num. heavy atoms : | 12 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.11 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 42.44 |
TPSA : | 50.09 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.04 cm/s |
Log Po/w (iLOGP) : | 1.9 |
Log Po/w (XLOGP3) : | 1.75 |
Log Po/w (WLOGP) : | 1.34 |
Log Po/w (MLOGP) : | 1.28 |
Log Po/w (SILICOS-IT) : | 1.68 |
Consensus Log Po/w : | 1.59 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.18 |
Solubility : | 1.07 mg/ml ; 0.00661 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.42 |
Solubility : | 0.614 mg/ml ; 0.00381 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.55 |
Solubility : | 0.455 mg/ml ; 0.00282 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.47 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302 | 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 |
---|---|---|
81% | With hydrazine hydrate In ethanol | Part A. 4-Cyanobenzoylhydrazine A mixture of methyl 4-cyanobenzoate(10.8 g, 67 mmol) and hydrazine monohydrate(18.6 g, 371 mmol) in absolute ethanol(70 ml) was heated to reflux for 3 hrs and then was allowed to cool down to rt. The solid portion was collected by filtration and washed with cold ethanol(20 ml) and then dried to give the product(8.7 g, 81percent yield). M.P.: 201° C. 1 H NMR(300 MHz, CDCl3) δ4.14(s, 2H), 7.40(s, 1H), 7.76(d, J=8, 2H), 7.88(d, J=8, 2H); MS(NH3 -CI) Calc. for (M+1)+: 162. Found: 162. |
80% | With hydrazine hydrate In methanol at 20℃; for 16 h; | (g) Preparation of 4-cyano-benzoic acid hydrazide 9:To a solution of 4-cyano-benzoic acid methyl ester (1.0 g, 13 mmol) in 30 mL of MeOH was added 3 mL of Η2ΝΝΗ22Ο. The mixture was stirred at ambient temperature for 16 h. The solid was collected and washed with CH3OH to give 4-cyano-benzoic acid hydrazide 9 as a solid. Yield: 0.8 g, 80percent..HNMR (DMSO-dg) δ (ppm): 7.93 (d, 4 H); 4.70 (s, 1 H); 3.30 (s, 2 H). |
76.7% | With hydrazine hydrate In methanol at 90℃; for 2 h; | Compound 1 (3g, 18.6mmol) was dissolved in MeOH (15ml) and NH2NH2-H2O (5.13g, 102.4mmol) was added. The mixture was stirred and raised to 900C for 2 hours. The mixture was concentrated and purified by chromatography to give desired product compound 2 as a white solid (2.3g). Yield: 76.7percent. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
58% | at 80℃; for 1 h; | Example 5: Synthesis of 3-[5-(4-Cyano-phenyl)-l,3,4-oxadiazol-2-ylmethyl]-N-((S)-6- morpholin-4-yl-4,5,6,7-tetrahydro-benzothiazol-2-yl)-benzamide (Compound 40) Add hydrazine monohydrate (5.50 mL, 110 mmol) to a solution of methyl 4-cyanobenzoate (3.30 g, 20.5 mmol) in 20 mL of EtOH. Heat the mixture at 80 °C for 1 h resulting in a solution. Cool the mixture to room temperature, causing a solid to precipitate from solution. Collect the precipitate by filtration, wash with cold EtOH followed by diethyl ether to provide 1.90 g, 58percent yield of 4-cyano-benzoic acid hydrazide as a light yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With hydroxylamine In methanol; tert-butyl methyl ether; water at 20 - 25℃; for 12.5 h; Large scale | A solution of methyl 4-cyanobenzoate (III) (2.50 kg, 1 wt) in methanol (7.5 L, 3 vol) was diluted with methyl tert.-butyl ether (9.3 kg, 3.7 wt). Aqueous hydroxylamine (50percent solution; 1 .23 kg, 0.5 wt, 1.2 eq.) was dosed over approximately 0.5 hours at 20-25°C. The dosing lines were rinsed with methanol (1 kg, 0.4 wt) and the reaction allowed to proceed for approximately 12 hours at 20-25°C. The batch was cooled to 5 ± 5°C and aged at 5 ± 5°C for 3 hours. The product, methyl 4-(N'-hydroxycarbamimidoyl)benzoate (IV), was isolated by filtration, washed with methyl tert.-butyl ether (2 x 5.5 kg, 2 x 2.2 wt), and dried under a flow of nitrogen at ambient for approximately 4 hours (2.38 kg, 93percent). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 50℃; for 15 h; | To a suspension of lithium aluminium hydride in tetrahydrofuran (400 mL) stirred in air at 0 °C was added a solution of methyl 4-cyanobenzoate (10 g, 62.1 mmol) in tetrahydrofuran (400 mL) dropwise over 15 minutes. The reaction mixture was stirred at 50 °C for 15 hours and then cooled to 0°C and quenched by the slow addition of water (7 mL), 15percent NaOH (7 mL), and water (21 mL). The resulting precipitate was stirred for an additional 30 minutes and filtered. The filtrated was concentrated in vacuo to give (4- (aminomethyl)phenyl)methanol (6.8 g, 80percent yield) as a light yellow oil. LCMS m/z = 138.0 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
76% | Stage #1: With trimethylaluminum; ammonium chloride In hexane; toluene at 0 - 80℃; Stage #2: With methanol In hexane; toluene at 20℃; for 1 h; |
6.64 g (124 mmol, 2 equiv. ) ammonium chloride are suspended in 100 ml of dry toluene under an argon atmosphere, and the mixture is cooled to 0°C. 62 ml (124 mmol, 2 equiv. ) of a 2M solution of trimethylaluminium in hexane are added dropwise, and the reaction mixture is stirred at room temperature until no more evolution of gas is observed. After addition of 10.0 g (62 mmol, 1 equiv. ) methyl 4- cyanobenzoate, the mixture is stirred at 80°C bath temperature over night. It is then cooled down to 0°C, and 50 ml of methanol are added with consequent stirring for 1 hour at room temperature. After filtration, the solid is washed with methanol for several times, the solution is evaporated to dryness in vacuo and the residue washed with methanol. Yield: 8.5 g (76percent) LC/MS (B): MS (ESI): 145 (M+H) +, retention time 0.33 min. |
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