[ CAS No. 479079-15-7 ] {[proInfo.proName]}

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Quality Control of [ 479079-15-7 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 479079-15-7 ]

CAS No. :	479079-15-7	MDL No. :	MFCD11052410
Formula :	C₇H₁₅N₃O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	189.21	Pubchem ID :	-
Synonyms :

Safety of [ 479079-15-7 ]

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Precautionary Statements:	P261-P280-P301+P312-P302+P352-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 479079-15-7 ]

* 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.

Downstream synthetic route of [ 479079-15-7 ]

[ 479079-15-7 ] Synthesis Path-Downstream 1~7

1
[ 85363-04-8 ]
[ 479079-15-7 ]

Yield	Reaction Conditions	Operation in experiment
66%	With hydroxylamine hydrochloride; sodium carbonate; In water; for 4h;Cooling with ice;	Hydroxylamine hydrochloride (2.7 g, 38.4 mmol), sodium carbonate (10.6 g, 96.0 mmol) were dissolved in100 ml of water, under ice-cooling, compound 1-1 (5.0 g, 32.0 mmol) was added dropwise to the system and stirred4 hours, after the end of the reaction, extracted with ethyl acetate, washed with saturated brine, dried over anhydrous sodium sulfate, and concentratedPurification by silica gel column gave compound 1-2 (4.0 g, 66.0%).
65%	With hydroxylamine hydrochloride; sodium carbonate; In methanol; water; at 90℃; for 23h;Reflux;	To a solution of Na2CO3(8.48 g, 0.08 mol, 1 equiv.) in water (35 mL) was slowly added a solution of hydroxylamine hydrochloride (5.56 g, 0.08 mol, 1 equiv.) in water (35 mL). The aqueous solution of hydroxylamine was added to a solution of the <strong>[85363-04-8]N-(tert-butoxycarbonyl)-2-aminoacetonitrile</strong> (12.5 g, 0.08 mol, 1 equiv.) in methanol (200 mL). The clear light yellow solution was heated at reflux (90C) overnight (23 h) with more water (100 mL) being added as necessary to dissolve the precipitate formed. The methanol was removed under reduced pressure, and the residue partitioned between ethyl acetate (100 mL) and water (100 mL). The aqueous phase was extracted with ethyl acetate, and the combined organic phase was dried over magnesium sulfate. The solvent was removed in vacuo to give a white powder. Yield 9.83 g, 65%; m.p. 147-148C; deltaH (MeOH-d6) 1.44 (9H, s, O'Bu), 3.64 (2H, s, CH2); deltaC(MeOH-d6) 158.8, 154.7, 80.7, 41.4, 28.7; LC-MS-EI 190.2 (MH+, 100); Found (CI) 190.11879 C7H15N3O3 (MH+) requires 190.11916.
	With ethanol; water; hydroxylamine; potassium carbonate; for 48h;Heating / reflux;	Description 22: (N-Hvdroxvcarbamimidovlmethvl) carbamic acid ter-butyl ester To a solution of N- (tert-butoxycarbonyl)-2-aminoacetonitrile (20. 0g) in absolute ethanol (200moi) was added a solution of hydroxylamine (9. 0g) and potassium carbonate (17. 6g) in water (50ml). The solution was heated to reflux for 2 days. The absolute ethanol was removed in vacuo and the aqueous residue extracted with ethyl acetate. The solvent was partially removed in vacuo until a precipitate formed. The suspension was cooled and filtered. The residue was washed with ethyl acetate to give the title compound as a white solid (12. 84g). Thermospray Mass Spectrum m/z 190 [MH+].

Reference： [1]Patent: CN106831747,2017,A .Location in patent: Paragraph 0076; 0077; 0078; 0079
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 2694 - 2707
[3]Patent: WO2011/61469,2011,A1 .Location in patent: Page/Page column 24
[4]Patent: WO2003/82861,2003,A2 .Location in patent: Page/Page column 47

2
[ 85363-04-8 ]
[ 479079-15-7 ]

Yield	Reaction Conditions	Operation in experiment
95%	With hydroxylamine; In ethanol; water; at 80℃;	N-(ter/-butoxycarbonyl)-2-aminoacetonitrile (4 g, 25.6 mmol) was dissolved in 10 ml ethanol and an aqueous solution of 50% hydroxylamine (2.36 ml, 38.4 mmol) was added. The reaction was heated at 800C overnight. The solvent was removed under vacuum and the residue was extracted with DCM. The combined DCM layers were dried over sodium sulfate and evaporated to yield Compound 31.1 (4.62 g, 95%) as an off-white solid. 1H NMR (400 MHz, DMSO-^6) ppm 1.37 (m, 9 H) 3.48 (d, J=6.36 Hz, 2 H) 5.22 (m, 2 H) 6.94 (t, J=5.87 Hz, 1 H) 8.97 (m, 1 H).
	With sodium hydroxide; hydroxylamine hydrochloride; In ethanol; water; for 30h;	Example 1.1.57: (5-methyl-l,2,4-oxadiazol-3-yl)methanamine; To a stirred solution of N-Boc-2-aminoacetonitrile (3.Og, 19.21 mmol) in a 4:1 mixture of EtOH and water (25mL) were added NaOH (860mg, 21.5mmol) and hydroxylamine hydrochloride 9 1.44g, 20.7mmol) and the reaction was stirred for 3Oh. All the solvent was evaporated under reduced pressure. The solid was dissolved in water and the aqueous layer was extracted with EtOAc. The combined organic layers were dried on Na2SO4 and concentrated to provide 1.8g of (Z) -tert-butyl 2-amino-2-(hydroxyimino)ethylcarbamate.
	With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; water; for 30h;	[0281] To a stirred solution of N-Boc-2-aminoacetonitrile (3.0g, 19.21 mmol) in a 4: 1 mixture of EtOH and water (25mL) were added NaOH (860mg, 21.5mmol) andhydroxylamine hydrochloride 9 1.44g, 20.7mmol) and the reaction was stirred for 30h. All the solvent was evaporated under reduced pressure. The solid was dissolved in water and the aqueous layer was extracted with EtOAc. The combined organic layers were dried on Na2S04 and concentrated to provide 1.8g of (Z)-tert-butyl 2-amino-2- (hydroxyimino)ethylcarbamate.

With hydroxylamine hydrochloride; sodium hydroxide; In ethanol; water; for 30h;

To a stirred solution of N-Boc-2-aminoacetonitrile (3.0g, 19.21 mmol) in a 4:1 mixture of EtOH and water (25mL) were added NaOH (860mg, 21.5mmol) andhydroxylamine hydrochloride 9 1.44g, 20.7mmol) and the reaction was stirred for 30h. All the solvent was evaporated under reduced pressure. The solid was dissolved in water and the aqueous layer was extracted with EtOAc. The combined organic layers were dried on Na2S04 and concentrated to provide 1.8g of (Z)-tert-butyl 2-amino-2-(hydroxyimino)ethylcarbamate.

Reference： [1]Patent: WO2008/5457,2008,A2 .Location in patent: Page/Page column 78
[2]Tetrahedron Letters,2008,vol. 49,p. 5133 - 5136
[3]Patent: WO2009/42694,2009,A1 .Location in patent: Page/Page column 97
[4]Patent: WO2011/130383,2011,A1 .Location in patent: Page/Page column 82
[5]Patent: WO2012/54510,2012,A1 .Location in patent: Page/Page column 83

3
[ 5470-11-1 ]
[ 85363-04-8 ]
[ 479079-15-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In ethanol; water; for 48h;Heating / reflux;	To a stirred solution of N-Boc-2-amino-acetonitrile (4.32 g) at r.t. in ethanol (40 ml) under an argon atmosphere were added H2O (10 ml), hydroxylamine hydrochloride (1.92 g) and potassium carbonate (3.82 g). The mixture (soon turning to a clear solution) was heated to reflux and stirring was continued for 2 days. The mixture was cooled to r.t. and the ethanol was removed in vacuo.The brown residue was diluted with H2O and extracted with EtOAc. The combined organics were washed with brine, dried, filtered and concentrated. The crude (N-hydroxycarbamimidoylmethyl)-carbamic acid tert-butyl ester (3.74 g) was used in the next step without further purification. White solid. MS 190.4 ([M+H]30 )

Reference： [1]Patent: US2008/103143,2008,A1 .Location in patent: Page/Page column 7

4
[ 479079-15-7 ]
[ 4498-67-3 ]
[ 1151512-97-8 ]

Yield	Reaction Conditions	Operation in experiment
92%	Stage #1: 1H-Indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl [2-amino-2-(hydroxyimino)ethyl]carbamate In N,N-dimethyl-formamide at 20℃; for 18h; Inert atmosphere;
92%	Stage #1: 1H-Indazole-3-carboxylic acid With 1,1'-carbonyldiimidazole In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: tert-butyl [2-amino-2-(hydroxyimino)ethyl]carbamate In N,N-dimethyl-formamide at 20℃;	2 To a round bottomed flask was added indazole-3-carboxylic acid (21.09 g, 0.13 mol, 1 equiv.) in DMF (500 mL) under nitrogen. Carbodiimidazole (CD1) (23.19 g, 0.14 mol, 1.1 equiv.) was added to the resulting slightly yellow solution and this was stirred at room temperature for 30 minutes. N-(tert-butoxycarbonyl)-2- ari-inoacetamidoxime from production Example 1 (27.06 g, 0.14 mol, 1.1 equiv.) in DMF (100 mL) was then added and the solution was stirred overnight at room temperature. The solvent was removed in vacuo on a high vacuum pump, and the crude solid was dissolved in dichloromethane. The resulting precipitate was filtered off to give a beige powder (39.6 g, 92%) which was dried in vacuo, m.p. 185-186°C; δΗ (MeOH-d6) 1.47 (9H, s, O'Bu), 3.86 (2H, s, CH2), 7.33 (1H, tJ7.9 Hz, ArH), 7.50 (1H, tJ6.9 Hz, ArH), 7.65 (1H, dJ8.5 Hz, ArH), 8.23 (1H, dJ8.2 Hz, ArH); δC (DMSO-d6) 161.3, 157.6, 155.8, 140.8, 134.9, 126.6, 122.6, 122.1, 121.1, 110.9, 78.4, 40.9, 28.1; LC-MS-EI (MH+, 100); Found (FAB) 356.13284 C15H19N5O4Na (M+Na) requires 356.13347.

Reference： [1]Location in patent: experimental part Clutterbuck, Lisa A.; Posada, Cristina Garcia; Visintin, Cristina; Riddall, Dieter R.; Lancaster, Barrie; Gane, Paul J.; Garthwaite, John; Selwood, David L. [Journal of Medicinal Chemistry, 2009, vol. 52, # 9, p. 2694 - 2707]
[2]Current Patent Assignee: UNIVERSITY OF LONDON - WO2011/61469, 2011, A1 Location in patent: Page/Page column 24-25

5
[ 85363-04-8 ]
[ 479079-15-7 ]

Yield	Reaction Conditions	Operation in experiment
85%	With hydroxylamine; In ethanol; water; at 80℃; for 1.5h;	Intermediate 641 ,1 -Dimethylethyl [2-(hydroxyamino)-2-iminoethyl]carbamateA flask was charged with 1 ,1 -dimethylethyl (cyanomethyl)carbamate (1 .562 g, 10 mmol) then filled with ethanol (15 mL) and hydroxylamine (50% w/w in water, 2.451 mL, 40.0 mmol) and the resulting mixture was stirred at 80C for 1 .5 h then cooled to room temperature and concentrated in vacuo. The residue was dissolved in DCM and the organic phase was dried using a phase separator then concentrated in vacuo. Trituration of the residue in Et20 gave 1 ,1 -dimethylethyl [2-(hydroxyamino)-2-iminoethyl]carbamate (1 .8 g, 9.51 mmol, 95 % yield) as a white solid which was used in the next step without further purification.
	With hydroxylamine; In ethanol; water; at 80℃; for 1.5h;	A flask was charged with 1,1-dimethylethyl (cyanomethyl)carbamate (1.562 g, 10 mmol) then filled with ethanol (15 mL) and hydroxylamine (50% w/w in water, 2.451 mL, 40.0 mmol) and the resulting mixture was stirred at 80 C. for 1.5 h then cooled to room temperature and concentrated in vacuo. The residue was dissolved in DCM and the organic phase was dried using a phase separator then concentrated in vacuo. Trituration of the residue in Et2O gave 1,1-dimethylethyl [2-(hydroxyamino)-2-iminoethyl]carbamate (1.8 g, 9.51 mmol, 95% yield) as a white solid which was used in the next step without further purification.

Reference： [1]Patent: WO2011/54841,2011,A1 .Location in patent: Page/Page column 72-73
[2]Patent: US2012/208798,2012,A1 .Location in patent: Page/Page column 32

6
[ 479079-15-7 ]
[ 1077-96-9 ]
[ 1309446-90-9 ]

Yield	Reaction Conditions	Operation in experiment
75%		To a round bottomed flask was added 5-Fluoro-lH-indazole-3-carboxylic acid from Production Example 4 (2.73 g, 0.015 mol, 1 equiv.) in DMF (40 mL) under nitrogen. Carbodiimidazole (CDI) (2.98 g, 0.018 mol, 1.1 equiv.) was added to the resulting yellow solution and this was stirred at room temperature for 30 minutes. N-(tert- butoxycarbonyl)-2-aminoacetarnidoxime (3.46 g, 0.018 mol, 1.1 equiv.) in DMF (20 mL) was then added and the solution was stirred overnight at room temperature. The solvent was removed in vacuo on a high vacuum pump, and the crude solid was dissolved in dichloromethane. The resulting precipitate was filtered off and dried in in vacuo to give a light brown powder (4.04 g, 75%); LC-MS-EI 352.4(MH+, 100).

Reference： [1]Patent: WO2011/61469,2011,A1 .Location in patent: Page/Page column 35

7
[ 4021-11-8 ]
[ 479079-15-7 ]
C₁₄H₁₈N₄O₃ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
19.6%	With N-ethyl-N,N-diisopropylamine; HATU; In dimethylsulfoxide-d6; at 20℃; for 2h;	Compound (1-2 g, 21.1 mmol), 2-methylpyridine-4-carboxylic acid (2.9 g, 21.1 mmol)N, N-diisopropylethylamine (11.0 ml, 63.3 mmol), 2- (7-azobenzotriazole) -N, N, N ', N'-tetramethyl(9.7 g, 11.5 mmol) was dissolved in 150 ml of dry dimethylsulfoxide and stirred at room temperature2 hours, the end of the reaction to the system by adding ice water 200ml, extracted with ethyl acetate, saturated salt waterWashed with anhydrous sodium sulfate, concentrated and purified by silica gel column to give compound 1-3 (1.1 g, 19.6%).

Reference： [1]Patent: CN106831747,2017,A .Location in patent: Paragraph 0076; 0080; 0081; 0082

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[ CAS No. 479079-15-7 ] {[proInfo.proName]}

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[ 479079-15-7 ] Synthesis Path-Downstream 1~7

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