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CAS No. : | 950739-21-6 | MDL No. : | MFCD22199259 |
Formula : | C3H4BrN3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VGBYIGUWAWHQOT-UHFFFAOYSA-N |
M.W : | 161.99 | Pubchem ID : | 46179974 |
Synonyms : |
|
Num. heavy atoms : | 7 |
Num. arom. heavy atoms : | 5 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 1.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 30.69 |
TPSA : | 54.7 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) : | -6.66 cm/s |
Log Po/w (iLOGP) : | 0.69 |
Log Po/w (XLOGP3) : | 0.89 |
Log Po/w (WLOGP) : | 0.76 |
Log Po/w (MLOGP) : | 0.21 |
Log Po/w (SILICOS-IT) : | 1.23 |
Consensus Log Po/w : | 0.75 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 2.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.93 |
Solubility : | 1.89 mg/ml ; 0.0117 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.62 |
Solubility : | 3.86 mg/ml ; 0.0238 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.72 |
Solubility : | 3.1 mg/ml ; 0.0191 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 1.89 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H320-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 |
---|---|---|
69% | With 1-propanephosphonic acid cyclic anhydride; N-ethyl-N,N-diisopropylamine In dichloromethane; ethyl acetate at 20℃; for 2h; | N-(3-Bromo-1H-pyrazol-5-yl)-3-(4-chlorophenyl)propanamide To a solution of 3-bromo-1H-pyrazol-5-amine (100 mg, 0.62 mmol, 1.0 equiv) in DCM (3.0 mL, 0.21 M) was added 3-(4-chlorophenyl)propanoic acid (150 mg, 0.81 mmol, 1.3 equiv), T3P (50% w/w in EtOAc, 300 mg, 0.81 mmol, 1.3 equiv), DIPEA (200 mL, 1.7 mmol, 2.7 equiv). After the addition, the mixture was stirred at rt for 2 h. The reaction mixture was concentrated in vacuo and purified by silica gel column chromatography (15-100% EtOAc in hexanes) to afford N-(3-bromo-1H-pyrazol-5-yl)-3-(4-chlorophenyl)propanamide (140 mg, 0.43 mmol, 69% yield) as a white solid. LCMS: ESI-MS m/z: 328.1 [M+H]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
73% | In glacial acetic acid at 80℃; for 8h; | 2-Bromo-7-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine (6) To a solution of 4 (18 g, 0.10 mmol) in 50 mL acetic acid was added 3-bromo-1H-pyrazol-5-amine (5) (19.8 g, 0.12 mmol), and reaction mixture was stirred at 80 oC for 8 hours, after the reaction completed, the cooled mixture was deposited dropwise in water, and the precipitate solid was filtered, dried to provide pure intermediate 6, as 20.5 g with 73% yield as off white solid. MP: 132-134°C; 1H NMR (400 MHz, DMSO-d6): δ 6.95 (d, 1H, J = 4.6 Hz), 7.34 (s, 1H), 7.65 (d, 2H, J = 6.2 Hz), 8.52 (d, 1H, J = 4.6 Hz), 8.67 (d, 2H, J = 6.2 Hz); 13C NMR (75 MHz, DMSO-d6): δ 118.5, 120.4, 121.8, 131.5, 132.6, 132.8, 148.3, 151.4, 153.2; HRMS (ESI): m/z calculated for C11H8 N4Br [M+H]+ 274.9932, found 274.9924.. |
73% | In glacial acetic acid at 80℃; for 8h; | 2-Bromo-7-(pyridin-4-yl)pyrazolo[1,5-a]pyrimidine (6) To a solution of 4 (18 g, 0.10 mmol) in 50 mL acetic acid was added 3-bromo-1H-pyrazol-5-amine (5) (19.8 g, 0.12 mmol), and reaction mixture was stirred at 80 oC for 8 hours, after the reaction completed, the cooled mixture was deposited dropwise in water, and the precipitate solid was filtered, dried to provide pure intermediate 6, as 20.5 g with 73% yield as off white solid. MP: 132-134°C; 1H NMR (400 MHz, DMSO-d6): δ 6.95 (d, 1H, J = 4.6 Hz), 7.34 (s, 1H), 7.65 (d, 2H, J = 6.2 Hz), 8.52 (d, 1H, J = 4.6 Hz), 8.67 (d, 2H, J = 6.2 Hz); 13C NMR (75 MHz, DMSO-d6): δ 118.5, 120.4, 121.8, 131.5, 132.6, 132.8, 148.3, 151.4, 153.2; HRMS (ESI): m/z calculated for C11H8 N4Br [M+H]+ 274.9932, found 274.9924.. |
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