[ CAS No. 10489-74-4 ] {[proInfo.proName]}

Name: 10489-74-4|Ethyl 2-(hydroxyamino)-2-iminoacetate|98%
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SKU: A178014
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Quality Control of [ 10489-74-4 ]

COA NMR CNMR HPLC LC-MS

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SDS Specification

Alternatived Products of [ 10489-74-4 ]

Product Details of [ 10489-74-4 ]

CAS No. :	10489-74-4	MDL No. :	MFCD03013442
Formula :	C₄H₈N₂O₃	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	-
M.W :	132.12	Pubchem ID :	-
Synonyms :

Calculated chemistry of [ 10489-74-4 ]

Physicochemical Properties

Num. heavy atoms :	9
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.5
Num. rotatable bonds :	3
Num. H-bond acceptors :	4.0
Num. H-bond donors :	2.0
Molar Refractivity :	29.75
TPSA :	84.91 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	No
P-gp substrate :	No
CYP1A2 inhibitor :	No
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-6.68 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.23
Log Po/w (XLOGP3) :	0.6
Log Po/w (WLOGP) :	-0.7
Log Po/w (MLOGP) :	-0.56
Log Po/w (SILICOS-IT) :	-0.87
Consensus Log Po/w :	-0.26

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	2.0
Bioavailability Score :	0.55

Water Solubility

Log S (ESOL) :	-0.84
Solubility :	19.1 mg/ml ; 0.145 mol/l
Class :	Very soluble
Log S (Ali) :	-1.96
Solubility :	1.46 mg/ml ; 0.011 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	0.51
Solubility :	431.0 mg/ml ; 3.27 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	4.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	1.97

Safety of [ 10489-74-4 ]

Signal Word:	Danger	Class:	4.1
Precautionary Statements:	P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:	1325
Hazard Statements:	H315-H319-H228	Packing Group:	Ⅲ
GHS Pictogram:

Application In Synthesis of [ 10489-74-4 ]

* 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 [ 10489-74-4 ]
Downstream synthetic route of [ 10489-74-4 ]

[ 10489-74-4 ] Synthesis Path-Upstream 1~2

1
[ 10489-74-4 ]
[ 75-98-9 ]
[ 158154-63-3 ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 100℃;	3.10.2 Preparation of ethyl 5-(tert-butyl)-1,2,4-oxadiazole-3-carboxylate (949-4) To a stirred solution of ethyl 2-(hydroxyamino)-2-iminoacetate (5.0 g, 37.8 mmol) in DMF (60 mL) were added pivalic acid (3.86 g, 37.8 mmol), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) (7.97 g, 41.58 mmol), HOBt (6.12 g, 45.3 mmol) and DIPEA (19.7 mL, 113.4 mmol). After being stirred at room temperature overnight, the reaction mixture was heated up to 100° C. for hr before cooled down to room temperature and partitioned between EA and H₂O. The layers were separated and the aqueous layer was extracted with EA (3*). The combined organic layers were washed with brine and dried over Na₂SO₄. The solvents were removed and the residue was purified by flash chromatography (silica gel, 10˜90percent ethyl acetate in petroleum ether) to provide ethyl 5-(tert-butyl)-1,2,4-oxadiazole-3-carboxylate (949-4) (1.8 g, 24percent) as a yellow solid. LC-MS: ESI m/z (M+1)=199.36.

Reference： [1] Patent: US2018/194762, 2018, A1, . Location in patent: Paragraph 0810

2
[ 10489-74-4 ]
[ 79-04-9 ]
[ 1009620-97-6 ]

Yield	Reaction Conditions	Operation in experiment
17%	With pyridine In chloroform at 0 - 20℃; for 1.08333 h;	To an ice cold suspension of ethyl 2-oximino-oxamate (1.17 g, 8.86 mmol) in chloroform (20 ml) was added pyridine (0.788 ml, 9.74 mmol) followed by chloroacetyl chloride (0.776 ml, 9.74 mmol) dropwise over 5 min. Upon completion of the addition the suspension was allowed to warm to room temperature and stirred for 1 h. The suspension was poured onto a mixture of DCM and water, the layers separated and the aqueous extracted with DCM (note: this resulted in a lot of precipitate that would not dissolve). The organic phase was washed with water and brine, dried (MgSO₄) and evaporated. The solid residue (-900 mg) was dissolved in AcOH (8 ml) and heated at reflux for 1 h. After this time, the hot solution was poured onto a mixture of EtOAc and satd. Na₂CO₃ (aq.) and the layers separated. The <n="77"/>organic layer was washed with further satd. Na₂CO₃ (aq.) (x2), water and brine, dried (MgSO₄) and evaporated to give the title compound as a brown oil (0.29 g, 17percent).

Reference： [1] Patent: WO2008/23157, 2008, A1, . Location in patent: Page/Page column 45; 74-75

[ 10489-74-4 ] Synthesis Path-Downstream 1~28

1
[ 10489-74-4 ]
[ 122-51-0 ]
[ 39512-59-9 ]

Yield	Reaction Conditions	Operation in experiment
79%	boron trifluoride diethyl etherate; at 20.0℃; for 1.5h;Heating / reflux;	To a suspension of ethyl 2-(hydroxyamino)-2-iminoacetate (3 g, 22.71 mmol) in triethylorthoformate (14 mL, 84.08 mmol) was added boron trifluoride diethyl etherate (0.144 mL, 1.14 mmol). It was heated for 90 minutes. The reaction mixture was concentrated under reduced pressure and the residue dissolved in chloroform. The resulting organic layer was washed with aqueous hydrochloric acid 2N (2x80 mL), aqueous sodium bicarbonate 4% (1x80 mL) and water (2x80 mL), it was dried over anhydrous sodium sulphate and the solvent removed under reduced pressure to yield the title compound (2.70 g, 79%) as a yellow oil.

Reference： [1]Patent: WO2008/107125,2008,A1 .Location in patent: Page/Page column 56-57
[2]Journal of Medicinal Chemistry,1967,vol. 10,p. 208 - 211

2
[ 506-68-3 ]
[ 10489-74-4 ]
[ 144167-51-1 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 6335 - 6360

3
[ 10489-74-4 ]
[ 922-67-8 ]
[ 144167-58-8 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 6335 - 6360

4
[ 623-49-4 ]
[ 10489-74-4 ]
[ 25475-06-3 ]

Reference： [1]Tetrahedron,1992,vol. 48,p. 6335 - 6360

5
[ 13831-03-3 ]
[ 10489-74-4 ]
[ 177417-73-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine;	Example 260 Synthesis of 4-(tert-butyl) 2-ethyl 1H-imidazole-2,4-dicarboxylate. To a mixture of <strong>[10489-74-4]ethyl (Z)-2-amino-2-(hydroxyimino)acetate</strong> (660 mg, 5 mmol) and tert-butyl propiolate (694 mg, 5.5 mmol) in Xylene (10 mL) was added TEA (606 mg, 6 mmol). The mixture was stirred at 140 C. for 16 h. After cooled to RT, H2O (25 mL) was added and the mixture was extracted with EtOAc (35 mL*3). The combined organic layers were washed with brine and dried over Na2SO4, concentrated to give the crude, which was purified by silica gel chromatography (PE/EA=1/1) to give 4-(tert-butyl) 2-ethyl 1H-imidazole-2,4-dicarboxylate (400 mg, yield: 33%) as a yellow solid. ESI-MS [M+H]+: 241.1.

Reference： [1]Bioorganic and Medicinal Chemistry Letters,2000,vol. 10,p. 1133 - 1137
[2]Patent: US2019/284182,2019,A1

6
[ 39520-24-6 ]
[ 10489-74-4 ]
5-(1-methoxycarbonyl-3-methyl-butyl)-[1,2,4]oxadiazole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2006,vol. 47,p. 4271 - 4274

7
[ 1694-31-1 ]
[ 10489-74-4 ]
ethyl 5-(2-oxopropyl)-1,2,4-oxadiazole-3-carboxylate [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 2231 - 2235

8
[ 10489-74-4 ]
[ 620-79-1 ]
5-(1-benzyl-2-oxo-propyl)-[1,2,4]oxadiazole-3-carboxylic acid ethyl ester [ No CAS ]

Reference： [1]Tetrahedron Letters,2007,vol. 48,p. 2231 - 2235

9
[ 10489-74-4 ]
[ 762-42-5 ]
(Z)-2-(Ethoxycarbonecarboximidoyl-aminooxy)-but-2-enedioic acid dimethyl ester [ No CAS ]

Reference： [1]Journal of Medicinal Chemistry,2007,vol. 50,p. 2225 - 2239

10
[ 10489-74-4 ]
[ 79-04-9 ]
[ 1009620-97-6 ]

Yield	Reaction Conditions	Operation in experiment
17%	With pyridine; In chloroform; at 0 - 20℃; for 1.08333h;	To an ice cold suspension of ethyl 2-oximino-oxamate (1.17 g, 8.86 mmol) in chloroform (20 ml) was added pyridine (0.788 ml, 9.74 mmol) followed by chloroacetyl chloride (0.776 ml, 9.74 mmol) dropwise over 5 min. Upon completion of the addition the suspension was allowed to warm to room temperature and stirred for 1 h. The suspension was poured onto a mixture of DCM and water, the layers separated and the aqueous extracted with DCM (note: this resulted in a lot of precipitate that would not dissolve). The organic phase was washed with water and brine, dried (MgSO4) and evaporated. The solid residue (-900 mg) was dissolved in AcOH (8 ml) and heated at reflux for 1 h. After this time, the hot solution was poured onto a mixture of EtOAc and satd. Na2CO3 (aq.) and the layers separated. The <n="77"/>organic layer was washed with further satd. Na2CO3 (aq.) (x2), water and brine, dried (MgSO4) and evaporated to give the title compound as a brown oil (0.29 g, 17%).

Reference： [1]Patent: WO2008/23157,2008,A1 .Location in patent: Page/Page column 45; 74-75

11
[ 10489-74-4 ]
[ 79-04-9 ]
[ 1049705-55-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	With diisopropylamine; In dichloromethane; at -10 - 20℃;	Step 1. Diiisopropylamine (21.6 ml.) was added dropwise to a stirred suspension of amino-[(Z)-hydroxyimino]-acetic acid ethyl ester (15 g) in dry DCM (300 ml.) cooled to - 1 O0C. After stirring for 10 minutes a solution of chloroacetyl chloride (9.96 ml_) in dry DCM (30 ml_) was added dropwise over 20 minutes to the cooled mixture. After stirring at room temperature overnight, the reaction was poured into ice/water mixture (1 L) to obtain two layers. Filtration of the bottom layer gave a brown precipitate which was washed with EtOAc (50 mL) and dried in vacuo to give amino-{N-[chloroacetate]imino}- acetic acid ethyl ester (21.54 g, 91 %) as a cream solid. LCMS (Method 7): Rt 2.41 min, m/z 209 [MH]+.

Reference： [1]Patent: WO2008/99186,2008,A1 .Location in patent: Page/Page column 66

12
[ 10489-74-4 ]
[ 84358-13-4 ]
[ 1207268-08-3 ]

Yield	Reaction Conditions	Operation in experiment
49%		Ethyl (2Z)-amino(hydroxyimino)ethanoate (1.1 eq.) was added to a solution of TBTU (1.2 eq.), l-(tert-butoxycarbonyl)piperidine-4-carboxylic acid (1 eq.) and DIPEA (2 eq.) in DCM(0.2 M) at RT. The reaction mixture was stirred at RT overnight. After dilution with EtOAc, the organic phase was washed with sat. sol. NaHCO3 and dried (Na2SO4). Evaporation of the solvent under reduced pressure afforded a white solid which was diluted with THF (0.2 M). The resulting solution was treated with TBAF (0.5 eq.) and the reaction mixture was heated to reflux overnight. Then, the reaction mixture was diluted with EtOAc and washed with sat. sol. NaHCO3 and dried (Na2SO4). Evaporation of the solvent under reduced pressure gave a crude which was purified by by flash chromatography on silica using EtO Ac/Petroleum ether (1 :1) as solvent to afford (49%) the title compound as a brown oil. MS (ES+) CiSH23N3Os required: 325, found: 326(M+H)+.

Reference： [1]Patent: WO2010/13037,2010,A1 .Location in patent: Page/Page column 61

13
[ 157033-23-3 ]
[ 10489-74-4 ]
[ 1258517-58-6 ]

Yield	Reaction Conditions	Operation in experiment
45%	With N-ethyl-N,N-diisopropylamine; In dichloromethane; at -10 - 20℃; for 22.5h;	INTERMEDIATE 75 - PREPARATION OF (Z)-Ethyl 2-amino-2-(2-(2,5- difluorophenyl)acetoxyimino)acetate.; 2-(2,5-difluorophenyl)acetyl chloride was prepared by heating overnight a suspension of 2,5-difluorophenylacetic acid (0.865 g; 3.67 mmol) and thionyl chloride (1.34 ml 18.15 mmol) in chloroform (30 mL) at 80 0C. After evaporation of the solvent and the excess of the thionyl chloride under reduced pressure, the residue was dissolved in dried dichloromethane (10 mL). This solution was added to a suspension of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate (0.500 g; 3.67 mmol) and Lambda/,Lambda/-diisopropylethylamine (1.03 mL; 5.87 mmol) in dry dichloromethane (20 mL) cooled at -10 0C and stirred for 10 minutes. The mixture was stirred at room temperature for 23 h and poured into a mixture of ice/water. The white precipitate is filtered off and washed with dichloromethane and dried under reduced pressure to afford 0.469 g (45%) of (Z)-ethyl 2-amino-2-(2-(2,5- difluorophenyl)acetoxyimino)acetate as a white solid. ESI/APCI (+) : 287 (M+H), 309 (M+Na). ESIAPCK-) : 285 (M-H).

Reference： [1]Patent: WO2010/142801,2010,A1 .Location in patent: Page/Page column 170

14
[ 1266229-03-1 ]
[ 10489-74-4 ]
[ 1266230-37-8 ]

Yield	Reaction Conditions	Operation in experiment
		To a solution of 2-tert-butyl 3-methyl(3S,8aR)-hexahydropyrrolo[1,2-a]pyrazine-2,3(1H)-dicarboxylate (2.50 g) in a mixed solvent (25 mL) of tetrahydrofuran/water (4/1) was added lithium hydroxide monohydrate (553 mg), and the mixture was stirred with heating for 50 C. at 3 hr. The reaction mixture was allowed to cool to room temperature, ethyl(2Z)-amino(hydroxyimino)ethanoate (1.74 g), 1-hydroxybenzotriazole (1.19 g) and N-[3-(dimethylamino)propyl]-N'-ethylcarbodiimide hydrochloride (3.37 g) were added thereto, and the mixture was stirred at room temperature for 4 hr. The mixture was diluted with ethyl acetate (300 mL), and washed with water (50 mL). The organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. The residue was dissolved in toluene (25 mL), and the solution was heated under reflux for 12 hr. The reaction mixture was allowed to cool to room temperature, and concentrated. The residue was subjected to silica gel column chromatography (ethyl acetate/hexane=1/99?40/60), and the collected fractions were concentrated to give the title compound (1.88 g) as a colorless oil. LC-MS: 367.2 (MH+).1H NMR (DMSO-d6, 300 MHz): delta 1.14-1.26 (1H, m), 1.28-1.49 (12H, m), 1.54-1.70 (2H, m), 1.72-2.12 (3H, m), 2.44-2.55 (1H, m), 2.56-2.85 (1H, m), 2.87-2.98 (1H, m), 3.51-3.63 (1H, m), 3.99-4.11 (1H, m), 4.35-4.45 (2H, m), 5.50-5.68 (1H, m).

Reference： [1]Patent: US2011/34469,2011,A1 .Location in patent: Page/Page column 98

15
[ 623-49-4 ]
[ 10489-74-4 ]

Yield	Reaction Conditions	Operation in experiment
45%	With hydroxylamine hydrochloride; potassium carbonate; In dichloromethane; water; at 20℃; for 12h;	To ethyl cyanoformate (10 g, 101.01 mmol) was added NH2OH-HCl (8.4 g, 121.74 mmol), K2CO3 (19.9 g, 144.20 mmol), and CH2C12/H2O (100 mL). The resulting mixture was stirred for 12 hr at room temperature. The solids were filtered out and the filtrated was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 6 g (45%) of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate as a white solid. To a mixture of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate (1 g, 7.58 mmol) and tert-butyl propiolate (940 mg, 7.46 mmol) was added Et3N (765 mg, 7.57 mmol) and toluene (50 mL). The resulting solution was stirred at 140 0C for 1 min. The resulting mixture was washed with 50 mL of H2O and then was extracted with 3 x 50 mL of dichloromethane. The organic layers were combined and washed with 20 mL of brine, then dried over anhydrous sodium sulfate. Evaporated the solvents and the residue was purified onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 1.1 g (61%) of 5 -tert-butyl 2-ethyl lH-imidazole-2, 5-dicarboxylate as a yellow solid.
38%	With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; at 20℃; for 10h;	To a solution of ethyl cyanoformate 87 (4 g, 40 mmol) in the mixture of ethanol (43 mL) and water (27 mL), was added hydroxylamine hydrochloride (5.6 g, 80 mmol) and sodium carbonate (3.3 g, 40 mmol). The resulting mixture was stirred at room temperature for lOh. After completion of the reaction, the crude mixture was concentrated to dryness, the residue was extracted with methylene chloride ( 100 mL x 3) The combined organic phase were washed with brine , dried anhydrous Na2SC>4, filtered and concentrated to dryness to give title compound 88, (Z)-ethyl 2-amino-2-(hydroxyimino)acetate (2 g, 38% yield) without further purification. LC-MS (LC method 1): m/z 133 (M+l)+.
19%	With hydroxylamine hydrochloride; sodium carbonate; In ethanol; water; at 20℃;Inert atmosphere;	ethyl [(Z)-N-hydroxycarbamimidoyl]formate In a 250-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, 2-ethoxy-2-oxoacetonitrile (5 g, 50.46 mmol, 1.00 equiv) and sodium carbonate (8 g, 75.48 mmol, 1.50 equiv) was mixed in a mixture of ethanol (50 mL) and water (30 mL), to which was added hydroxylamine hydrochloride (5.2 g, 74.83 mmol, 1.48 equiv). The resulting mixture was stirred overnight at room temperature. After the reaction was done, the reaction mixture was concentrated under reduced pressure and the remaining solution was extracted with dichloromethane (3*30 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure to afford ethyl [(Z)-N-hydroxycarbamimidoyl]formate (1.3 g, 19%) as off-white solid. MS: m/z=133.0 [M+H]+.

Reference： [1]Patent: WO2009/139834,2009,A1 .Location in patent: Page/Page column 151
[2]Patent: WO2017/189866,2017,A1 .Location in patent: Paragraph 0177
[3]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0402
[4]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 760 - 778
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 760 - 778,19

16
[ 13831-03-3 ]
[ 10489-74-4 ]
3H-imidazole-2,4-dicarboxylic acid 4-tert-butyl ester 2-ethyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With triethylamine; In toluene; at 140℃; for 0.0166667h;	To ethyl cyanoformate (10 g, 101.01 mmol) was added NH2OH-HCl (8.4 g, 121.74 mmol), K2CO3 (19.9 g, 144.20 mmol), and CH2C12/H2O (100 mL). The resulting mixture was stirred for 12 hr at room temperature. The solids were filtered out and the filtrated was concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 6 g (45%) of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate as a white solid. To a mixture of (Z)-ethyl 2-amino-2- (hydroxyimino)acetate (1 g, 7.58 mmol) and tert-butyl propiolate (940 mg, 7.46 mmol) was added Et3N (765 mg, 7.57 mmol) and toluene (50 mL). The resulting solution was stirred at 140 0C for 1 min. The resulting mixture was washed with 50 mL of H2O and then was extracted with 3 x 50 mL of dichloromethane. The organic layers were combined and washed with 20 mL of brine, then dried over anhydrous sodium sulfate. Evaporated the solvents and the residue was purified onto a silica gel column with ethyl acetate/petroleum ether (1 :1), resulted in 1.1 g (61%) of 5 -tert-butyl 2-ethyl lH-imidazole-2, 5-dicarboxylate as a yellow solid.

Reference： [1]Patent: WO2009/139834,2009,A1 .Location in patent: Page/Page column 151

17
[ 10489-74-4 ]
[ 5744-59-2 ]
[ 693-13-0 ]
[ 1403333-49-2 ]

Yield	Reaction Conditions	Operation in experiment
	With pyridine;	a) Ethyl 5-(1,5-dimethyl-1H-pyrazol-3-yl)-1,2,4-oxadiazole-3-carboxylate Ethyl aminohydroxyiminoacetate (3.78 mmol, 0.5 g), <strong>[5744-59-2]1,5-dimethyl-1H-pyrazole-3-carboxylic acid</strong> (95%, 3.78 mmol, 0.530 g) and 1,3-diisopropylcarbodiimide (4.16 mmol, 0.525 g) were suspended in DCM (70 ml) under nitrogen atmosphere. The mixture was stirred at RT for a day. The solvent was evaporated and pyridine was added to the residue. The resulting mixture was refluxed for 6 h and stirred at RT overnight. Pyridine was evaporated and the residue diluted with DCM and water. The phases were separated and the water phase was extracted four times with DCM. The combined organics were washed with aqueous HCl solution, saturated NaHCO3, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.285 g of the title compound was obtained. 1H-NMR (400 MHz, MeOH-d4): delta 1.43 (t, 3H), 2.30 (s, 3H), 4.23 (s, 3H), 4.49 (q, 2H), 6.96 (s, 1H).

Reference： [1]Patent: US2014/94474,2014,A1 .Location in patent: Page/Page column

18
[ 10489-74-4 ]
[ 3209-71-0 ]
[ 693-13-0 ]
[ 1343187-68-7 ]

Yield	Reaction Conditions	Operation in experiment
	In pyridine;	a) Ethyl 5-(isoxazol-3-yl)-1,2,4-oxadiazole-3-carboxylate Ethyl aminohydroxyiminoacetate (3.78 mmol, 0.5 g), <strong>[3209-71-0]3-<strong>[3209-71-0]isoxazolecarboxylic acid</strong></strong> (3.78 mmol, 0.428 g) and 1,3-diisopropylcarbodiimide (4.16 mmol, 0.525 g) were dissolved in DCM (70 ml) under nitrogen atmosphere. The mixture was stirred at RT for a day. The solvent was evaporated to dryness and the residue was dissolved in pyridine and refluxed for 6 h and overnight at RT. Pyridine was evaporated and the residue was diluted with DCM and water. The aqueous phase was extracted four times with DCM. The combined organics were washed with aqueous HCl solution, saturated NaHCO3, water and brine. The organic phase was dried, filtered and evaporated. The crude product was purified by flash chromatography. 0.396 g of the title compound was obtained. Rotamers were obtained in 1H-NMR and analysis was repeated at elevated temperature. 1H-NMR (400 MHz, DMSO-d6, +60 C.): delta 1.38 (t, 3H), 4.49 (q, 2H), 7.21 (d, 1H), 9.05 (d, 1H).

Reference： [1]Patent: US2014/94474,2014,A1 .Location in patent: Page/Page column

19
[ 10489-74-4 ]
[ 4023-34-1 ]
ethyl 5-cyclopropyl-1,2,4-oxadiazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
26%		Ethyl 5-cyclopropyl-1,2,4-oxadiazole-3-carboxylate In a 25-mL round bottom flask, <strong>[10489-74-4]ethyl [(Z)-N-hydroxycarbamimidoyl]formate</strong> (500 mg, 3.78 mmol, 1.00 equiv) and DIEA (978 mg, 7.57 mmol, 2.00 equiv) were mixed in dichloromethane (5 mL), to which was added cyclopropanecarbonyl chloride (393 mg, 3.76 mmol, 0.99 equiv) dropwise at -15 C. The resulting solution was stirred for 16 h at room temperature. When the reaction was done, it was quenched by 10 mL water and the mixture was extracted with dichloromethane (3*5 mL). The organic layers were combined, dried over anhydrous sodium sulfate and concentrated under reduce pressure. The residue was then re-dissolved in pyridine (5 mL) at room temperature and the resulting solution was stirred for 16 h at 110 C. After the reaction was done, the reaction mixture was concentrated under reduced pressure and the residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (1% to 10% gradient) to afford ethyl 5-cyclopropyl-1,2,4-oxadiazole-3-carboxylate (180 mg, 26%) as yellow oil. MS: m/z=183.0 [M+H]+.

Reference： [1]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0359

20
[ 10489-74-4 ]
[ 4124-31-6 ]
[ 1351343-57-1 ]

Yield	Reaction Conditions	Operation in experiment
80%	In toluene; at 110℃;	Ethyl 5-(trichloromethyl)-1,2,4-oxadiazole-3-carboxylate In a 100-mL round bottom flask, trichloroacetyl 2,2,2-trichloroacetate (695 mg, 2.25 mmol, 1.00 equiv) and <strong>[10489-74-4]ethyl [(Z)-N-hydroxycarbamimidoyl]formate</strong> (300 mg, 2.27 mmol, 1.01 equiv) were dissolved in toluene (5 mL) at room temperature. The resulting solution was stirred overnight at 110 C. After the reaction was done, the reaction mixture was concentrated under reduced pressure, and then the residue was dissolved in 30 mL ethyl acetate and washed with brine (3*10 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to afford ethyl 5-(trichloromethyl)-1,2,4-oxadiazole-3-carboxylate (470 mg, 80%) as red oil.

Reference： [1]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0403

21
[ 30992-29-1 ]
[ 10489-74-4 ]
ethyl (2E)-2-(2-[[(tert-butoxy)carbonyl]amino]-2-methylpropanamido)-2-(hydroxyimino)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%	With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;Inert atmosphere;	Ethyl (2E)-2-(2-[[(tert-butoxy)carbonyl]amino]-2-methylpropanamido)-2-(hydroxyimino)acetate In a 50-mL round bottom flask purged and maintained with an inert atmosphere of nitrogen, <strong>[10489-74-4]ethyl [(Z)-N-hydroxycarbamimidoyl]formate</strong> (820 mg, 6.21 mmol, 1.00 equiv) was dissolved in N,N-dimethylformamide (10 mL), to which were added HATU (3.54 g, 9.31 mmol, 1.50 equiv), DIEA (2.4 g, 18.57 mmol, 2.99 equiv) and 2-[[(tert-butoxy)carbonyl]amino]-2-methyl propanoic acid (1.26 g, 6.20 mmol, 1.00 equiv) at room temperature. The resulting solution was stirred overnight at room temperature. When the reaction was done, it was quenched by the addition of 10 mL water and the resulting mixture was extracted with dichloromethane (3*15 mL). The organic layers were combined, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified in a silica gel column eluting with ethyl acetate in petroleum ether (10% to 50% gradient) to afford ethyl (2E)-2-(2-[[(tert-butoxy)carbonyl]amino]-2-methylpropanamido)-2-(hydroxyimino)acetate (300 mg, 15%) as light yellow solid.

Reference： [1]Patent: US2016/96834,2016,A1 .Location in patent: Paragraph 0409

22
(1,3-dimethyl-4-oxo-1,4-dihydro-5h-pyrazolo[3,4-d]pyrimidin-5-yl)acetic acid hydrochloride salt [ No CAS ]
[ 10489-74-4 ]
ethyl 5-[(1,3-dimethyl-4-oxo-1,4-dihydro-5H-pyrazolo[3,4-d]pyrimidin-5-yl)methyl]-1,2,4-oxadiazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
98%	With 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In dichloromethane; N,N-dimethyl-formamide; at 20 - 120℃; for 2h;Microwave irradiation;	The title compound of PREPARATION 51(250 mg, 0.97 mmol) was dissolved in 10dichloroethane and 3 ml dimethylformamide. Ethyl (2Z)-amino(hydroxyimino)acetate (128 mg, 0.97 mmol) and N-(3-dimethylaminopropyl)-N?-ethylcarbodiimide hydrochloride (241 mg, 1.26 mmol) were added and the mixture was stirred at roomtemperature. After 1 h, the reaction was stirred at 120 C for lh under microwave irradiation. The mixture was allowed to cool and was partitioned between ethyl acetate and water. The aqueous phase was extracted with ethyl acetate. The organics were washed sequentially with water and brine, dried over anhydrous sodium sulphate, filtered and evaporated to give 301 mg (0.96 mmol, 98% yield) of the title compound.Purity 100%.

Reference： [1]Patent: WO2017/60488,2017,A1 .Location in patent: Page/Page column 77

23
[ 10489-74-4 ]
[ 4755-77-5 ]
[ 40019-27-0 ]

Yield	Reaction Conditions	Operation in experiment
> 99%	With pyridine; In chloroform; at 0 - 20℃; for 4.5h;Reflux;	A 1-l,three-neck flask equipped with a magnetic stir bar, refluxcondenser, drying tube, dropping funnel, and thermometerwas charged with ethyl 2-amino-2-(hydroxyimino)acetate(32)74 (32.0 g, 242 mmol) and CHCl3 (500 ml). Anhydrouspyridine (59.0 ml, 732 mmol) was added to the slurry, andthe reaction mixture was cooled with an ice bath (internaltemperature 5-10C). Ethyl chlorooxoacetate (40.6 ml,363 mmol) was added over a period of 1 h from thedropping funnel at such a rate to maintain the reactiontemperature around 10C. The cooling bath was removed,the reaction mixture was stirred at room temperature for30 min and then refluxed for 3 h. A fine precipitateimpurity was formed during reflux, which was filtered offafter cooling to room temperature. The CHCl3 solution wasdiluted with CH2Cl2 and washed successively with 1 N HCl(3×300 ml), H2O (2×300 ml), and brine (2×300 ml). Theorganic layer was dried with anhydrous Na2SO4, and theorganic solution concentrated to give product 33 that wasused in the next step without any further purification. Yield52 g (>99%), colorless oil. IR spectrum (ATR, neat), nu, cm-1:1752 (C=O). 1H NMR spectrum (600 MHz, CDCl3),delta, ppm: 4.67-4.41 (4H, m, 2CH2); 1.54-1.37 (6H, m,2CH3). 13C NMR spectrum (150 MHz, CDCl3), delta, ppm:167.7; 162.6; 156.5; 153.2; 64.3; 63.4; 14.0; 13.9.

Reference： [1]Chemistry of Heterocyclic Compounds,2017,vol. 53,p. 760 - 778
Khim. Geterotsikl. Soedin.,2017,vol. 53,p. 760 - 778,19

24
[ 10489-74-4 ]
[ 108-24-7 ]
(Z)-ethyl 2-(acetoxyimino)-2-aminoacetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
700 mg	at 20℃; for 0.5h;	A mixture of compound 88 (1 g, 7.5 mmol) and AC2O (5 mL) was stirred at room temperature for 30 min. The crude mixture was concentrated to give title compound 89, (Z)-ethyl 2-(acetoxyimino)-2-aminoacetate (700 mg), which used in the next step without purification.

Reference： [1]Patent: WO2017/189866,2017,A1 .Location in patent: Paragraph 0178

25
2-(3-chloroquinolin-6-yl)acetyl chloride [ No CAS ]
[ 10489-74-4 ]
ethyl 5-((3-chloroquinolin-6-yl)methyl)-1,2,4-oxadiazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
15%		To a solution of <strong>[10489-74-4](Z)-ethyl 2-amino-2-(hydroxyimino)acetate</strong> (209 mg, 1.58 mmol, 1.0 eq) and DIEA (612 mg, 4.74 mmol, 3.0eq) in DCM (20 mL) was added 2-(3- chloroquinolin-6-yl)acetyl chloride (380 mg, 1.58 mmol, 1.0 eq) at 0 C. The mixture was stirred at rt overnight. The solvent was evaporated, and pyridine (20 mL) was added and heated to 100 C for 12 h. The mixture was concentrated, and the resulting residue was purified by chromatography on a silica gel column (PE/EA = 3/1, v/v) to give ethyl 5-((3- chloroquinolin-6-yl)m ethyl)- l,2,4-oxadiazole-3-carboxylate (80 mg, 15%) as a white solid.

Reference： [1]Patent: WO2018/11628,2018,A1 .Location in patent: Paragraph 00200

26
[ 10489-74-4 ]
[ 75-98-9 ]
[ 158154-63-3 ]

Yield	Reaction Conditions	Operation in experiment
1.8 g	With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20 - 100℃;	3.10.2 Preparation of ethyl 5-(tert-butyl)-1,2,4-oxadiazole-3-carboxylate (949-4) To a stirred solution of ethyl 2-(hydroxyamino)-2-iminoacetate (5.0 g, 37.8 mmol) in DMF (60 mL) were added pivalic acid (3.86 g, 37.8 mmol), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) (7.97 g, 41.58 mmol), HOBt (6.12 g, 45.3 mmol) and DIPEA (19.7 mL, 113.4 mmol). After being stirred at room temperature overnight, the reaction mixture was heated up to 100 C. for hr before cooled down to room temperature and partitioned between EA and H2O. The layers were separated and the aqueous layer was extracted with EA (3*). The combined organic layers were washed with brine and dried over Na2SO4. The solvents were removed and the residue was purified by flash chromatography (silica gel, 10?90% ethyl acetate in petroleum ether) to provide ethyl 5-(tert-butyl)-1,2,4-oxadiazole-3-carboxylate (949-4) (1.8 g, 24%) as a yellow solid. LC-MS: ESI m/z (M+1)=199.36.

Reference： [1]Patent: US2018/194762,2018,A1 .Location in patent: Paragraph 0810

27
[ 16480-05-0 ]
[ 10489-74-4 ]
ethyl (Z)-2-amino-2-(((1-methylcyclopropane-1-carbonyl)oxy)imino)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
3 g	With triethylamine; In dichloromethane; at 20℃; for 2h;	To a solution of 1-methylcyclopropane-1-carboxylic acid (2 g, 20 mmol) in DCM (50 mL) was added (coCl)2 (5 g, 40 mmol). The mixture was stirred at rt for 16 h and then concentrated to give the intermediate acyl chloride. To a solution of ethyl (Z)-2-amino-2- (hydroxyimino)acetate (2.6 g, 20 mmol) and triethylamine (6 g, 60 mmol) in DCM (20 mL) was added a solution of the intermediate acyl chloride in DCM (20 mL). The reaction was stirred at rt for 2 h, washed by water, dried by Na2SO4, concentrated to give ethyl (Z)-2-amino-2-(((1- methylcyclopropane-1-carbonyl)oxy)imino)acetate as a white solid (3.0 g, yield: 63%). ESI-MS (M+H) +: 215.1.

Reference： [1]Patent: WO2018/191577,2018,A1 .Location in patent: Page/Page column 130; 135

28
[ 1427082-88-9 ]
[ 10489-74-4 ]
ethyl 5-(5-cyano-4-methylpyridin-2-yl)-1,2,4-oxadiazole-3-carboxylate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
44.90%	With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine; In ethyl acetate; at 0 - 70℃; for 18h;	To a stirred solution of Intermediate 187A (0.70 g, 4.32 mmol) in EtOAc (25 mL) was added TEA (2.41 mL, 17.27 mmol), <strong>[10489-74-4]ethyl (Z)-2-amino-2-(hydroxyimino)acetate</strong> (0.07 g, 5.18 mmol) followed by 1-propanephosphonic anhydride (5.49 g, 8.63 mmol) at 0 oC and the resulting reaction mixture was heated at 70 C for 18 h. The reaction mixture was diluted with water (50 mL) and extracted with EtOAc (3 x 50 mL). The combined organic layers were washed with brine (50 mL), dried over anhydrous sodium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography (Redisep-24 g, 35% EtOAc/n-Hexane) to obtain Intermediate 187B (0.50 g, 44.90%).1H NMR (400 MHz, CDCl3) G ppm 1.51 (t, J = 7.03 Hz, 3 H), 2.66 - 2.77 (s, 3 H), 4.59 (q, J = 7.36 Hz, 2 H), 8.39 (s, 1 H), 9.00 (s, 1 H). LCMS (Method-I) retention time 1.39 min, [M+H] 259.3

Reference： [1]Patent: WO2018/222795,2018,A1 .Location in patent: Page/Page column 311

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