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CAS No. : | 93439-79-3 | MDL No. : | MFCD00141526 |
Formula : | C10H11N3O | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | KMQAYHNPVNGXMQ-UHFFFAOYSA-N |
M.W : | 189.21 | Pubchem ID : | 2766938 |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.1 |
Num. rotatable bonds : | 2 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 54.92 |
TPSA : | 63.93 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) : | -6.41 cm/s |
Log Po/w (iLOGP) : | 1.19 |
Log Po/w (XLOGP3) : | 1.47 |
Log Po/w (WLOGP) : | 1.68 |
Log Po/w (MLOGP) : | 0.98 |
Log Po/w (SILICOS-IT) : | 1.8 |
Consensus Log Po/w : | 1.42 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.39 |
Solubility : | 0.773 mg/ml ; 0.00409 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.42 |
Solubility : | 0.721 mg/ml ; 0.00381 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.52 |
Solubility : | 0.0567 mg/ml ; 0.0003 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.85 |
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: |
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* 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 |
---|---|---|
88.1 The title compound is prepared as described in example 1, (Stage 1.4 and 1.2); using (4-methoxy-phenyl)-acetonitrile instead. White crystals; mp. 198-201° C.; MS(ESI+):m/z=190 (M+H)+; HPLC: AtRet=2.85 minutes (System1). | ||
95.88.1 Stage 88.1: 4-(4-Methoxy-phenyl)-2H-pyrazol-3-ylamine Stage 88.1: 4-(4-Methoxy-phenyl)-2H-pyrazol-3-ylamine The title compound is prepared as described in example 8, (Stage 1.4 and 1.2); using (4-methoxy-phenyl)-acetonitrile instead. White crystals; mp. 198-201° C.; MS(ESI+):m/z=190 (M+H)+; HPLC: AtRET=2.85 minutes (System1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With potassium phosphate In 1,4-dioxane at 100℃; for 15h; | 17 Example 17; Preparation of Compound 16; A tube containing a stir bar was charged with a solution of 4-(4-methoxy- phenyl)-2H-pyrazol-3-ylamine (0.10 mmol), Pd2(DBA)3 (5.0 μmol, 4.6 mg), Xantphos (0.010 mmol, 5.8 mg) and Compound A (0.050 mmol, 23 mg) in dioxane (1 mL). To the solution was then added K3PO4 (0.10 mmol, 21 mg) and the reaction tube was flushed with N2 then sealed tightly. The resulting reaction was heated to 100 °C and allowed to stir at this temperature for about 15 hours, then cooled to room temperature. The reaction mixture was then diluted with acetonitrile (5 mL), the EPO resulting solution was centrifuged for about 2 hours at a speed of about 1000 rpm, and the supernatant was collected and concentrated in vacuo. To the resulting residue was added TFA (0.5 mL) and the resulting solution was allowed to stand for 10 minutes, then concentrated in vacuo. The resulting residue was purified using reverse phase HPLC to provide Compound 16. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: sodium / 20 - 50 °C 2: hydrazine hydrate; acetic acid / toluene / 3 h / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With acetic acid at 110℃; Sealed tube; | 82.3 Step 3. 5-(2,3-Dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one A solution of 4-(4-methoxyphenyl)-1H-pyrazol-5-amine (189 mg, 1.00 mmol, 1.00 equiv) in acetic acid (2 mL) was placed into an 8-mL tube. Then ethyl 3-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-oxopropanoate (289 mg, 1.156 mmol, 1.1 equiv, 90%) was added and the tube was sealed. The reaction was stirred overnight at 110° C. Then the reaction was concentrated in vacuo to dryness. The residue was diluted with 5 mL of methanol and the resulting solids were collected by filtration, and washed with methanol. Drying afforded 240 mg (63%) of 5-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)-3-(4-methoxyphenyl)pyrazolo[1,5-a]pyrimidin-7(4H)-one as a white solid. LC-MS: (ES, m/z): 376 [M+H]+ 1H-NMR (300 MHz, DMSO, ppm): δ 11.97 (s, 1H), 8.08 (s, 1H), 7.55 (d, J=8.1 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
52% | With hydrazine hydrate; acetic acid In toluene for 3h; Reflux; | 82.2 Step 2. 4-(4-Methoxyphenyl)-1H-pyrazol-5-amine A solution of 2-(4-methoxyphenyl)-3-oxopropanenitrile (1.75 g, 10.00 mmol, 1.00 equiv) in toluene (30 mL) was placed into a 100-mL round-bottom flask. Then N2H4H2O (1 g, 20.00 mmol, 2.00 equiv) and acetic acid (2.1 g, 35.00 mmol, 3.50 equiv) were added. The resulting reaction was heated to reflux for 3 hrs. The reaction was concentrated in vacuo and diluted with 5 ml of MeOH. The resulting solid was filtered and washed with methanol. The solid was dried in an oven in vacuo. This resulted in 1.0 g (52%) of 4-(4-methoxyphenyl)-1H-pyrazol-5-amine as a yellow solid. LC-MS: (ES, m/z): 190 [M+H]+ 1H-NMR (300 MHz, DMSO, ppm): δ 11.60 (s, 1H), 7.58 (s, 1H), 7.43 (d, J=8.7 Hz, 2H), 6.92 (d, J=8.7 Hz, 2H), 4.61 (s, 2H), 3.75 (s, 3H) |
With hydrazine hydrate In methanol at 160℃; for 0.166667h; Microwave irradiation; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrazine hydrate; acetic acid In ethanol at 50℃; for 7h; Overall yield = 70 %; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | In methanol at 150℃; for 0.416667h; Microwave irradiation; regioselective reaction; | General method for the synthesis of 5-aza-9-deaza-adenines 6. General procedure: A mixture of 5-aminopyrazole 4 (1.3 mmol), cyanamide (63.3 mg, 1.5 mmol) and triethylorthoformate (0.3 mL, 2.3 mmol) in MeOH (2 mL) was irradiated in a 10mL seamless pressure vial using a CEM Discover microwave synthesizer operating at maximal microwave power up to 150 W at 150 °C for 25 min. After cooling, the precipitated product 6 was filtered, washed with cold MeOH and dried under vacuum. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
72% | With montmorillonite |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: montmorillonite 2: ammonium cerium (IV) nitrate / acetone / 4 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | In acetic acid for 0.166667h; Reflux; | 3-[3-(4-Methoxyphenyl)-5-methylpyrazolo[1,5-a]pyrimidin-6-yl]-5-[4-(pyridin-2-yl)piperazin-1-yl]-1,2,4-thiadiazole (9b) A solution of enaminone 3b (3.58 g, 0.01 mol) and 4-(4-methoxyphenyl)-1H-pyrazol-5-amine (8b) (2.08 g, 0.011 mol) in acetic-acid was refluxed for 10 min. A precipitate formed after cooling was filtered, washed with isopropyl alcohol, and dried in vacuo.The yield was 2.90 g (60%). M.p. 175-176 °C. 1H NMR(DMSO-d6), δ: 2.20 (s, 3 H, CH3); 3.25-3.40 (m, 8 H, 4 CH2);3.70 (s, 3 H, CH3O); 6.77 (t, 1 H, H Py, J = 7.2 Hz); 6.90 (d, 1 H,H Py, J = 7.2 Hz); 7.10 (m, 2 H, H arom); 7.45 (t, 1 H, HPy, J = 7.3 Hz);8.10 (m, 2 H, H arom); 8.20 (d, 1 H, H Py, J = 7.2 Hz); 8.70(s, 1 H, CH); 9.23 (s, 1 H, CH). 13C NMR (DMSO-d6), δ:15.23, 43.80, 48.27, 55.15, 107.50, 109.97, 113.53, 113.58,114.21, 124.18, 127.13, 137.75, 137.81, 143.03, 146.91, 147.67,149.91, 157.87, 158.49, 165.67, 184.22. MS, m/z (Irel (%)): 484[M]+ (100), 469 (5), 364 (6), 351 (6), 335 (5), 264 (8), 249 (11),66 (6). Found (%): C, 63.49; H, 5.01; N, 24.59. C24H24N8S.Calculated (%): C, 63.42; H, 4.98; N, 24.65. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | Stage #1: 5-amino-4-(4-methoxyphenyl)-1Н-pyrazole With hydrogenchloride; sodium nitrite In water Stage #2: ethyl acetoacetate With sodium acetate In water at 20℃; for 1h; | 12 5.6. General procedure for the synthesis of compounds 7c-f, 7h-p General procedure: The suitable 4-substituted-5-aminopyrazoles (1c-f, 1h-p) (20 mmoles) were diazotized as usual and the solution of diazonium salt was treated with of sodium acetate (24 mmoles) at room temperature and stirred until to complete dissolution. At this solution was then added ethyl acetoacetate (20.0 mmoles) in ethanol and stirred for 1 h at room temperature. The final compounds were recovered by filtration after addition of water or by extraction if a precipitate was not formed. Starting from 1f, in this reaction condition, a byproduct is formed and identified as 1H-Benzo[h]pyrazolo[3,4-c]cinnoline, 10. The unambiguous synthesis of this latter was obtained as described below. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: hydrogenchloride; sodium nitrite / water 1.2: 1 h / 20 °C 2.1: piperidine / toluene / 90 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: hydrogenchloride; sodium nitrite / water 1.2: 1 h / 20 °C 2.1: piperidine / toluene / 90 °C 3.1: hydrazine hydrate; sodium acetate; acetic acid / Reflux |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1.1: tetrahydrofuran / 0.03 h / 0 - 20 °C 1.2: 0.08 h / 100 °C / Microwave irradiation; Sealed tube 2.1: sodium hydroxide / tetrahydrofuran / 0.05 h / 80 °C / Sealed tube; Microwave irradiation 3.1: tetrahydrofuran / 0.25 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: tetrahydrofuran / 0.03 h / 0 - 20 °C 1.2: 0.08 h / 100 °C / Microwave irradiation; Sealed tube 2.1: sodium hydroxide / tetrahydrofuran / 0.05 h / 80 °C / Sealed tube; Microwave irradiation |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Stage #1: Ethoxycarbonyl isothiocyanate; 5-amino-4-(4-methoxyphenyl)-1Н-pyrazole In tetrahydrofuran at 0 - 20℃; for 0.0333333h; Stage #2: In tetrahydrofuran at 100℃; for 0.0833333h; Microwave irradiation; Sealed tube; | 3.2.1. Synthesis of 2-Thioxo-1H-pyrazolo[1,5-a][1,3,5]triazin-4-one (3a) General procedure: In a microwave vial, ethoxycarbonyl isothiocyanate (1.0 equiv.) was added dropwiseto a solution of 5-aminopyrazole 1a-n (1.0 equiv.) in dry THF (3 mL) at 0 °C. Aftercomplete addition, the mixture was stirred 2 min at room temperature and the vial wassealed, deposited in a microwave reactor and heated at 100 °C for 5 min. After cooling,NaOH 2N (2.0 equiv.) was added and the vessel was sealed again and irradiated at 80 °Cfor 3 min. After cooling, the resulting aqueous solution was acidified (pH < 5) with HCl2N then the precipitate was filtered off, washed with water up to neutral pH, trituratedwith Et2O then DCM and dried under vacuum to give 3a (4.601 g, 94%) as a white solid(4.601 g, 94%) from 1a (2.5 g, 29.20 |