PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE CAS#: 159326-68-8; 凯望编码 (ChemWhat Code): 549058

IdentificationPhysical DataSpectra
Route of Synthesis (ROS)Safety and HazardsOther Data

Identification

英文名PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE
IUPAC Namepyrrolo[2,1-f][1,2,4]triazin-4-amine
分子结构Structure of Pyrrolo[1,2-f][1,2,4]triazin-4-amine CAS 159326-68-8
CAS编号 159326-68-8
EINECS NumberNo data available
MDL NumberNo data available
Beilstein Registry NumberNo data available
别名159326-68-8
4-aminopyrrolo<2,1-f><1,2,4>triazine,
pyrrolo[2,1-f ][1,2,4]-triazin-4-amine,
4-aminopyrrolo[2,1-f][1,2,4]-triazine,
pyrrolo[2,1-f][1,2,4]-triazin-4-amine,
4-aminopyrrolo[2,1-f][1,2,4]triazine,
pyrrolo[2,1-f][1,2,4]triazin-4-amine, pyrrolo[2,1-f][1,2,4]triazin-4-ylamine
CAS No: 159326-68-8
CAS: 159326-68-8
CAS Number: 159326-68-8
分子式C6H6N4
分子量134.139
InChIInChI=1S/C6H6N4/c7-6-5-2-1-3-10(5)9-4-8-6/h1-4H,(H2,7,8,9)
InChI KeyVSPXQZSDPSOPRO-UHFFFAOYSA-N
Canonical SMILESc1cc2c(ncnn2c1)N
Patent Information
No data available

Physical Data

AppearancePowder
SolubilityNo data available
Acidity coefficient (pKa)4.28±0.30(Predicted)
Flash PointNo data available
Refractive indexNo data available
SensitivityNo data available
Melting Point, °C Solvent (Melting Point)
236 – 239 H2O

Spectra

Description (NMR Spectroscopy)Nucleus (NMR Spectroscopy)Solvents (NMR Spectroscopy)Temperature (NMR Spectroscopy), °C Original Text (NMR Spectroscopy) Comment (NMR Spectroscopy)
1Hd(4)-methanol 19.84 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) Signals given
1Hd(4)-methanol 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) Signals given
Chemical shifts1Hdimethylsulfoxide-d6, D2O
Chemical shifts13Cdimethylsulfoxide-d6, D2O
Spin-spin coupling constants 1H-1H.
Description (Mass Spectrometry)
LCMS (Liquid chromatography mass spectrometry), ESI (Electrospray ionisation)
LCMS (Liquid chromatography mass spectrometry), ESI (Electrospray ionisation)
Description (UV/VIS Spectroscopy)Solvent (UV/VIS Spectroscopy)Comment (UV/VIS Spectroscopy)Absorption Maxima (UV/VIS), nmExt./Abs. Coefficient, l·mol-1cm-1
Absorption maxima234, 272

Route of Synthesis (ROS)

Route of Synthesis (ROS) of PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE CAS 159326-68-8
Route of Synthesis (ROS) of PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE CAS 159326-68-8
ConditionsYield
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at -20℃; for 1.5h;

Experimental Procedure
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, 5%CH3OH/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 5% 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 Magnesol and concentrated in vacuo to afford crude mono-bromide, KRAM 206-3-1 , 29.9 g, 90% 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 % 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 1.5h;

Experimental Procedure
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, 5%CH3OH/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 5% 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, 90% 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 % 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]. 		90%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at -20℃; for 1.5h; regioselective reaction;

Experimental Procedure
Synthesis of 7-bromopyrrolo[2,1-f][1,2,4]triazin-4-amine:
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 % 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 %). 		77%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at -20℃; for 1h;

Experimental Procedure
A Step A. 7-Bromopyrrolo[2, 1 -fill ,2,4ltriazin-4-amine.
To a solution of pyrrolo[2, 1- f][l,2,4]triazin-4-amine (2.1 g, 15.66 mmol, 1.00 equiv) in DIVIF (20 mL) was added 1,3- dibromo-5,5-dimethylimidazolidine-2,4-dione (2.24 g, 7.83 mmol, 0.53 equiv) at -20 °C in batches. The resulting solution was stirred for 1 h at -20 °C, then quenched by the addition of 30 mL of sat. sodium sulfite (aq). After filtration, the filter was dissolved in 200 ml of ethyl acetate, washed with 100 mL of sat. sodium carbonate (aq.), dried over sodium sulfate and concentrated under reduced pressure. This resulted in 2.50 g (75%) of the title compound as a white solid. MS mlz [M+H]b (ESI): 213, 215. 		75%
With 1,3-dibromo-5,5-dimethylimidazolidine-2,4-dione In N,N-dimethyl-formamide at -40 – 0℃; for 0.75h;

Safety and Hazards

Pictogram(s)No data available
SignalNo data available
GHS Hazard StatementsNo data available
[Warning Hazardous to the aquatic environment, long-term hazard]
Information may vary between notifications depending on impurities, additives, and other factors.
Precautionary Statement CodesNo data available
(The corresponding statement to each P-code can be found at the GHS Classification page.)
For more detailed information, please visit ECHA C&L website
Source: European Chemicals Agency (ECHA)
License Note: Use of the information, documents and data from the ECHA website is subject to the terms and conditions of this Legal Notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the ECHA website may be reproduced, distributed and/or used, totally or in part, for non-commercial purposes provided that ECHA is acknowledged as the source: “Source: European Chemicals Agency, http://echa.europa.eu/”. Such acknowledgement must be included in each copy of the material. ECHA permits and encourages organisations and individuals to create links to the ECHA website under the following cumulative conditions: Links can only be made to webpages that provide a link to the Legal Notice page.
License URL: https://echa.europa.eu/web/guest/legal-notice
Record Name: (1-Cyano-2-ethoxy-2-oxoethylidenaminooxy)dimethylamino-morpholino-carbenium hexafluorophosphate
URL: https://echa.europa.eu/information-on-chemicals/cl-inventory-database/-/discli/details/213446
Description: The information provided here is aggregated from the “Notified classification and labelling” from ECHA’s C&L Inventory. Read more: https://echa.europa.eu/information-on-chemicals/cl-inventory-database

Other Data

TransportationNo data available
Under the room temperature and away from light
HS Code294200
StorageUnder the room temperature and away from light
Shelf Life1 year
Market PriceUSD
Druglikeness
Lipinski rules component
分子量134.14
logP0.97
HBA4
HBD1
Matching Lipinski Rules4
Veber rules component
Polar Surface Area (PSA)56.21
Rotatable Bond (RotB)0
Matching Veber Rules2
Bioactivity
In vitro: Efficacy
Quantitative Results
pXParameterValue (qual)Value (quant)UnitTargetEffect
4.06Kd (dissociation constant) =88µM Mitogen-activated protein kinase kinase kinase kinase 4 [human]:Wildbinding activity
8.05Activity(Ligand efficiency) =0.56Mitogen-activated protein kinase kinase kinase kinase 4 [human]:Wildbinding activity
Use Pattern
PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE CAS#: 159326-68-8 is used as Remdesivir Intermediates.

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