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Quality Control of Zanamivir impurity F Purity: 97% SDS Specification

COA

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NMR

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CNMR

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HPLC

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Product Details of Zanamivir impurity F

CAS No. :	4023-02-3
Formula :	C₄H₇ClN₄
M.W :	146.58
SMILES Code :	N=C(N1N=CC=C1)N.[H]Cl
Synonyms :	1H-Pyrazole-1-carboximidamide hydrochloride
MDL No. :	MFCD00210087
InChI Key :	RBZRMBCLZMEYEH-UHFFFAOYSA-N
Pubchem ID :	2734672

Safety of Zanamivir impurity F

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P305+P351+P338

Application In Synthesis of Zanamivir impurity F

* 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.

Upstream synthesis route of [ 4023-02-3 ]
Downstream synthetic route of [ 4023-02-3 ]

[ 4023-02-3 ] Synthesis Path-Upstream 1~1

1
[ 501-53-1 ]
[ 4023-02-3 ]
[ 152120-62-2 ]

References: [1] Tetrahedron Letters, 1993, vol. 34, # 21, p. 3389 - 3392.
[2] Journal of Medicinal Chemistry, 2008, vol. 51, # 24, p. 8168 - 8172.

[ 4023-02-3 ] Synthesis Path-Downstream 1~18

1
[ 24424-99-5 ]
[ 4023-02-3 ]
[ 152120-61-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With potassium carbonate; In water; acetone; at 20℃;	To a solution of di-tert-butyldicarbonate (13.4 g, 61.5 mmol) in acetone (45 mL) were added lH-pyrazole-l-carboxamidine hydrochloride (9.0 g, 61.5 mmol, 1.0 equiv.) and 9.0 mL of water. K2CO3 (4.24 g, 30.6 mmol, 0.5 equiv.) in H20 (12.0 mL) was added dropwise for 30 min at room temperature. After 2 h, another portion of di-tert- butyldicarbonate (1.35 g, 6 mmol, 0.1 equiv.) was added and the solution was stirred overnight. The acetone was removed under reduced pressure and the resulting white solid was dissolved in 30.0 mL of water, and allowed to stir at 0 C for 30 min. The precipitated tert-butyl (imino(lH-pyrazol-l-yl)methyl)carbamate was collected by filtration, washed with water, washed with hexane, and dried in vacuo to provide the title compound as a colorless solid (11.37 g, 88% yield). FontWeight="Bold" FontSize="10" H NMR (CDCI3, 400 MHz): delta 9.06 (brs, 1H), 8.45 (d, J= 3.2 Hz, 1H), 7.67 (d, J= 0.8 Hz, 1H), 7.59 (brs, 1H), 6.39 (dd, J = 2.8, 1.6 Hz, 1H), 1.54 (s, 9H).
74.8%	With dmap; triethylamine; In tetrahydrofuran; at 20℃; for 20h;	Step 1: Preparation of tert-butyl (1H-pyrazol-1-ylcarbonoimidoyl)carbamate To a solution of (Boc)2O (61 g, 0.28 mol) in THF (1 L) was added DMAP (17 g, 0.14 mol) and Et3N (42 g, 0.42 mol). After stirring for 30 min, 1H-pyrazole-1-carboximidamide hydrochloride (20 g, 0.14 mol) was added and the mixture was stirred at 20 C. for 20 hrs. The reaction was then concentrated in vacuo and the residue was dissolved in EtOAc (500 mL). The solution was washed with aq. NH4Cl (250 mL), dried over anhydrous Na2SO4, filtered and concentrated in vacuo. The residue was recrystallized from EtOAc (200 mL) to afford the title compound (22 g, 74.8% yield) as white solid that was used as-is in the next step.
	With N-ethyl-N,N-diisopropylamine; In hexane; dichloromethane; ethyl acetate;	Step 1 Manufacture of N-tert-butoxycarbonyl-pyrazole-1-carboxamidine To a solution of di-tert-butyl dicarbonate (7.43 g, 33 mmol) in 100 ml dichloromethane 11.3 ml of N,N-diisopropylethylamine (66 mmol) and 4.40 g of 1H-pyrazole-1-carboxamidine hydrochloride (30 mmol) were added. The solution was agitated for 3 h at room temperature and then evaporated to dryness. The obtained white solid was dissolved in 200 ml ethylacetate, the organic phase was washed with 5 % (w/w) sodium hydrogen carbonate, dried over magnesium sulfate and finally evaporated to dryness. The residue was dissolved in boiling hexane. The solution was allowed to stand at room temperature over night and then at 4C for 24 hours. The crystals thus formed were recovered by filtration and washed in cold hexane (0C). After drying, 5.28 g of white crystals were obtained (25 mmol yield=84 %).

References: [1]Tetrahedron Letters,2007,vol. 48,p. 2357 - 2359.
[2]Organic and Biomolecular Chemistry,2013,vol. 11,p. 3943 - 3948.
[3]Patent: WO2015/147950,2015,A2 .Location in patent: Page/Page column 38.
[4]Patent: US2013/79324,2013,A1 .Location in patent: Paragraph 0827; 0828.
[5]Tetrahedron Letters,1993,vol. 34,p. 3389 - 3392.
[6]Tetrahedron,2007,vol. 63,p. 9502 - 9513.
[7]Patent: EP945138,1999,A1 .

2
[ 29390-67-8 ]
[ 4023-02-3 ]
mono-6-deoxy-6-guanidinocycloheptaamylose [ No CAS ]

References: [1]Journal of the American Chemical Society,2018,vol. 140,p. 3959 - 3974.
[2]Journal of Organic Chemistry,1998,vol. 63,p. 1737 - 1739.

3
[ 141-43-5 ]
[ 4023-02-3 ]
[ 1458-01-1 ]
[ 2394-67-4 ]