PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE CAS#: 159326-68-8

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

Identification	Physical Data	Spectra
Route of Synthesis (ROS)	Safety and Hazards	Other Data

Identification

Structure of Pyrrolo[1,2-f][1,2,4]triazin-4-amine CAS 159326-68-8

Patent Information

No data available

Physical Data

Appearance	Powder
Solubility	No data available
Acidity coefficient (pKa)	4.28±0.30(Predicted)
Flash Point	No data available
Refractive index	No data available
Sensitivity	No 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)
	1H	d(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
	1H	d(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 shifts	1H	dimethylsulfoxide-d6, D2O
Chemical shifts	13C	dimethylsulfoxide-d6, D2O
Spin-spin coupling constants					1H-1H.

Description (Mass Spectrometry)

LCMS (Liquid chromatography mass spectrometry), ESI (Electrospray ionisation)

Description (UV/VIS Spectroscopy)	Solvent (UV/VIS Spectroscopy)	Comment (UV/VIS Spectroscopy)	Absorption Maxima (UV/VIS), nm	Ext./Abs. Coefficient, l·mol^-1cm^-1
Absorption maxima			234, 272

Route of Synthesis (ROS)

Conditions	Yield
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
Signal	No data available
GHS Hazard Statements	No 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 Codes	No 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)
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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

Transportation	No data available
	Under the room temperature and away from light
HS Code	294200
Storage	Under the room temperature and away from light
Shelf Life	1 year
Market Price	USD

Druglikeness
Lipinski rules component
Molecular Weight	134.14
logP	0.97
HBA	4
HBD	1
Matching Lipinski Rules	4
Veber rules component
Polar Surface Area (PSA)	56.21
Rotatable Bond (RotB)	0
Matching Veber Rules	2

Bioactivity

In vitro: Efficacy

Quantitative Results

pX	Parameter	Value (qual)	Value (quant)	Unit	Target	Effect
4.06	Kd (dissociation constant)	=	88	µM	Mitogen-activated protein kinase kinase kinase kinase 4 [human]:Wild	binding activity
8.05	Activity(Ligand efficiency)	=	0.56		Mitogen-activated protein kinase kinase kinase kinase 4 [human]:Wild	binding 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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Product Name	PYRROLO[1,2-F][1,2,4]TRIAZIN-4-AMINE
IUPAC Name	pyrrolo[2,1-f][1,2,4]triazin-4-amine
Molecular Structure
CAS Registry Number	159326-68-8
EINECS Number	No data available
MDL Number	No data available
Beilstein Registry Number	No data available
Synonyms	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
Molecular Formula	C₆H₆N₄
Molecular Weight	134.139
InChI	InChI=1S/C6H6N4/c7-6-5-2-1-3-10(5)9-4-8-6/h1-4H,(H2,7,8,9)
InChI Key	VSPXQZSDPSOPRO-UHFFFAOYSA-N
Canonical SMILES	c1cc2c(ncnn2c1)N