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CAS No. : | 159326-68-8 | MDL No. : | MFCD08234647 |
Formula : | C6H6N4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VSPXQZSDPSOPRO-UHFFFAOYSA-N |
M.W : | 134.14 | Pubchem ID : | 10441749 |
Synonyms : |
|
Num. heavy atoms : | 10 |
Num. arom. heavy atoms : | 9 |
Fraction Csp3 : | 0.0 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 37.39 |
TPSA : | 56.21 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.07 cm/s |
Log Po/w (iLOGP) : | 1.25 |
Log Po/w (XLOGP3) : | 0.07 |
Log Po/w (WLOGP) : | 0.32 |
Log Po/w (MLOGP) : | 0.39 |
Log Po/w (SILICOS-IT) : | -0.2 |
Consensus Log Po/w : | 0.37 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 1.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.38 |
Solubility : | 5.57 mg/ml ; 0.0415 mol/l |
Class : | Very soluble |
Log S (Ali) : | -0.8 |
Solubility : | 21.1 mg/ml ; 0.157 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -1.32 |
Solubility : | 6.41 mg/ml ; 0.0478 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.01 |
Signal Word: | Warning | Class: | |
Precautionary Statements: | P280-P305+P351+P338 | UN#: | |
Hazard Statements: | H317-H319 | Packing Group: | |
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 potassium phosphate In ethanol at 78℃; for 18 h; | To a stirred suspension of i-Amino-I H-pyrrole-2-carbonitrile hydrochloride (50 g, 0.35 mol) in absolute ethanol (800 ml.) was added formamidine acetate (181.3 g, 1.74 mol) .bul. and potassium phosphate- (370 g, 1.74 mol). The suspension was heated for 18 hours (at)5 78 0C (under N2), then cooled, filtered and concentrated to dryness in vacuo. The residue was mixed with ice water (2L) and the dark grayish-brown solids were collected by suction filtration. The filter cake was washed with water, sucked dry and the solids were dissolved (on the funnel) with hot ethyl acetate and filtered into a collection vessel. The dark solution was filtered through a long plug of 30/40 Magnesol and the pale yellow10 filtrate was concentrated to dryness in vacuo to afford a yellow-tinged solid (20.6 g, 44.1percent yield). The plug was washed with ethyl acetate/ethanol and the washings were concentrated in vacuo to afford additional material, 10.7 g (23percent). Extraction of the aqueous work-up filtrate with ethyl acetate followed by drying, Magnesol filtration and concentration gave another 6.3 g (14percent) of clean product, bringing the total recovery to15 37.6g (81percent). 1H-NMR (CD3OD): δ 7.72 (s, 1H), 7.52 (dd, 1H, J =2.5, 1.6 Hz), 6.85 (dd, 1H1 J= 4.5, 1.6 Hz), 6.64 (dd, 1 H, J= 4.5, 2.7 Hz) LC/MS (+esi): m/z=135.1 [M+H]. |
81% | With potassium phosphate In ethanol at 78℃; for 18 h; | To a stirred suspension of 1 -Amino- lH-pyrrole-2-carbonitrile hydrochloride (50 g, 0.35 mol) in absolute ethanol (800 mL) was added formamidine acetate (181.3 g, 1.74 mol) and potassium phosphate (370 g, 1.74 mol). The suspension was heated for 18 hours at 78 0C (under N2), then cooled, filtered and concentrated to dryness in vacuo. The residue was mixed with ice water (2L) and the dark grayish-brown solids were collected by suction filtration. The filter cake was washed with water, sucked dry and the solids were dissolved(on the funnel) with hot ethyl acetate and filtered into a collection vessel. The dark solution was filtered through a long plug of 30/40 Magnesol and the pale yellow filtrate was concentrated to dryness in vacuo to afford a yellow-tinged solid (20.6 g, 44.1percent yield). The plug was washed with ethyl acetate/ethanol and the washings were concentrated in vacuo to afford additional material, 10.7 g (23percent). Extraction of the aqueous work-up filtrate with ethyl acetate followed by drying, Magnesol filtration and concentration gave another 6.3 g (14percent) of clean product, bringing the total recovery to 37.6g (81percent). 1H-NMR (CD3OD): δ 7.72 (s, IH), 7.52 (dd, IH, J =2.5, 1.6 Hz), 6.85 (dd, IH, J = 4.5, 1.6 Hz), 6.64 (dd, IH, / = 4.5, 2.7 Hz) LC/MS (+esi): m/z=135.1 [M+H]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
90% | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at -20℃; for 1.5 h; | A stirred solution containing Intermediate A (21.0 g, 0.157 mol) in anhydrous DMF (200 ml_) was cooled to -20 0C and 1 ,3-dibromo-5,5-dimethylhydantoin (22.4 g, 0.078 mol) was added portionwise over -45 minutes. The reaction was stirred for another 45 minutes and monitored for completion by TLC (silica gel, GHLF, 5percentCH3OH/CH2Cl2). Saturated25 Na2SO3 solution (300 mL) was added, the resulting suspension was stirred and the solids were collected by suction filtration. The filter cake was washed with water, dried by suction and then partitioned between ethyl acetate (1 L) and 5percent sodium carbonate solution (1L). The layers were separated, the organic layer was washed with fresh sodium carbonate solution and dried over magnesium sulfate. The filtrate from the work-30 up was also extracted and combined with the main batch then filtered through a pad of <n="77"/>Magnesol and concentrated in vacuo to afford crude mono-bromide, KRAM 206-3-1 , 29.9 g, 90percent yield. Trituration of a 21.5 g quantity of the crude product in hot ethyl acetate (300 mL, 70 C) provided colorless solids (12.3 g) containing only ~2 percent of the di-brominated side-product. 1H-NMR (CD3OD) : δ 7.84 (s, 1 H), 6.95 (d, 1 H, J= 4.7 Hz), 6.71 (d, 1H, J = 4.7 Hz), 4.89 (s, 3H, -NH2 + H2O); MS: LC/MS (+esi), m/z = 213.1 [M+H]. |
90% | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at -20℃; for 1.5 h; | A stirred solution containing pyrrolo[2,l-f][l,2,4]triazin-4-ylamine (21.0 g, 0.157 mol) in anhydrous DMF (200 mL) was cooled to -20 0C and l,3-dibromo-5,5-dimethylhydantoin (22.4 g, 0.078 mol) was added portionwise over -45 minutes. The reaction was stirred for another 45 minutes and monitored for completion by TLC (silica gel, GHLF, 5percentCH3OH/CH2C12). Saturated Na2SO3 solution (300 mL) was added, the resulting suspension was stiired and the solids were collected by suction filtration. The filter cake was washed with water, dried by suction and then partitioned between ethyl acetate (IL) and 5percent sodium carbonate solution (IL). The layers were separated, the organic layer was washed with fresh sodium carbonate solution and dried over magnesium sulfate. The filtrate from the work-up was also extracted and combined with the main batch then filtered through a pad of Magnesol and concentrated in vacuo to afford crude mono-bromide, KRAM 206-3-1, 29.9 g, 90percent yield. Trituration of a 21.5 g quantity of the crude mono-/di-bromo product in hot ethyl acetate (300 mL, 70 0C) provided colorless solids (12.3 g) containing only ~2 percent of the di-brominated side-product. 1H-NMR (CD3OD): δ 7.84 (s, IH), 6.95 (d, IH, J = 4.7 Hz), 6.71 (d, IH, / = 4.7 Hz), 4.89 (s, 3H, -NH2 + H2O); MS: LC/MS (+esi), m/z = 213.1 [M+H]. |
77% | With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at -20℃; for 1.5 h; | A stirred solution containing pyrrolo[2,1-f][1,2,4]-triazin-4-amine (10 g, 75 mmol) in anhydrous N,N-dimethylformamide(100 mL) was cooled to -20 °C and 1,3-dibromo-5,5-dimethylhydantoin (10.7 g, 37.4 mmol) was added portionwise over 45 min. The reaction was stirred for another45 min and monitored by TLC. After completion, the reaction mixture was washed with saturated aqueous solution of sodium sulfite (150 mL) and water. It was then partitioned between ethyl acetate (0.5 L) and 5 percent aqueous solution of sodium carbonate (500 mL). The organic layer was washed with aqueous solution of sodium carbonate, dried and concentrated to afford 13.3 g crude product. It was purified by silica gel column chromatography (CH2Cl2:MeOH = 100:1) to give the7-bromo compound as a white crystal (12.3 g, 77 percent). |
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