1158970-52-5|Ethyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate| Ambeed

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Quality Control of [ 1158970-52-5 ] Purity: 98% SDS Specification

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Product Details of [ 1158970-52-5 ]

CAS No. :	1158970-52-5
Formula :	C₁₉H₁₈BrN₃O₂S
M.W :	432.33
SMILES Code :	O=C(CSC1=NN=C(N1C2=C3C=CC=CC3=C(C4CC4)C=C2)Br)OCC
MDL No. :	MFCD31692645
InChI Key :	IOUDSMHEYZSUQF-UHFFFAOYSA-N
Pubchem ID :	57811399

Safety of [ 1158970-52-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H335
Precautionary Statements:	P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501

Application In Synthesis of [ 1158970-52-5 ]

* 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 [ 1158970-52-5 ]

[ 1158970-52-5 ] Synthesis Path-Downstream 1~25

2
[ 1158970-52-5 ]
(-)-2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid [ No CAS ]

References: [1]Patent: CN105622531,2016,A .

3
[ 1158970-52-5 ]
C₁₉H₁₈BrN₃O₂S [ No CAS ]
C₁₉H₁₈BrN₃O₂S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
150 mg; 152 mg	With diethylamine; In ethanol; carbon dioxide;Supercritical conditions; Resolution of racemate; liquid CO2;	Compound 12 with reference to the patent or patent CN103524440A W2009070740 reported synthesized. Compound 12 (330.00mg,763.31umol) by supercritical fluid chromatography SFC (chiral column: ChiralpakAS (250mm × 30mm, 5um); mobile phase: supercritical CO2 /Ethanol (0.05% DEA) = 70/30; flow rate: 60mL / min; detection wavelength: 220nm) isolated compound 12A (150.00mg, 346.96umol) and Compound 12B (152.00mg, 351.58umol).

References: [1]Patent: CN105622531,2016,A .Location in patent: Paragraph 0085; 0086; 0087.

4
[ 1158970-52-5 ]
(+)-2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid [ No CAS ]

References: [1]Patent: CN105622531,2016,A .

5
[ 878671-95-5 ]
[ 1158970-52-5 ]

References: [1]Patent: CN105985295,2016,A .
[2]Patent: CN106866560,2017,A .

6
[ 1533519-86-6 ]
[ 1158970-52-5 ]

References: [1]Patent: CN105985295,2016,A .

7
C₁₅H₁₃N₃S [ No CAS ]
[ 1158970-52-5 ]

References: [1]Patent: CN105985295,2016,A .

8
[ 1533519-85-5 ]
[ 1158970-52-5 ]

References: [1]Patent: CN105985295,2016,A .

9
[ 25033-19-6 ]
[ 1158970-52-5 ]

References: [1]Patent: CN105985295,2016,A .

10
2-[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid [ No CAS ]
[ 64-17-5 ]
[ 1158970-52-5 ]

Yield	Reaction Conditions	Operation in experiment
95.4%	With sulfuric acid; at 5 - 25℃; for 145h;	Lesinurad, free form (0.25g), prepared according to W02009070740, purity 97.0 1% by HPLC analysis, was suspended in ethanol (1 .25mL) at 20C and the resulting slurry treated with sulfuric acid (75uL). The resulting solution was stirred for lh at 20C andthen temperature cycled between 5C and 25C for 144h. The solution was then concentrated on a rotary evaporator and the residue re-dissolved in dichloromethane (lOmL) and washed with sodium bicarbonate solution (lOmL). The layers were separated and the organic layer was washed with water (2x 1 OmL). The aqueous layer was then extracted with dichloromethane (2x 1 OmL) and the washings were combined with theorganic layer and dried over sodium sulfate. Evaporation of the dichloromethane yielded an oil (100% th. yield). The oil was analyzed by HPLC which indicated the presence of 95.4% lesinurad ethyl ester and 1.8% lesinurad, free form.
864 mg		At 5 ,Oxalyl chloride (257 mg, 2.0 mmol) was added over 5 min,Add dropwise to(-) Or (+) - 2- (5-bromo-4- (4-cyclopropyl-naphthalen-1-yl) -4H-1,2,4- triazol-3-ylthio) acetic acid (810mg , 2.0 mmol)In dichloromethane (10mL) in a solution.In the mixture was further stirred at 10 20 minutes,Ethanol was then added (dry, 1mL) at 0 ,Stir at room temperature for 20 minutes.The volatiles were removed under vacuum and the solvent type in 30 ,The residue was dissolved in 5 mL of ethanol,And concentrated under reduced pressure at 30 C,Then add 5mL ethanol,Diluted with 30 mL of re-distilled water,Lyophilizer lyophilized to give a solid (-) or (+) - 2- (5-bromo-4- (4-cyclopropyl-naphthalen-1-yl) -4H-1,2,4- triazol-3 Ylthio) acetic acidEthyl ester (864 mg),

References: [1]Patent: WO2017/36884,2017,A1 .Location in patent: Page/Page column 16.
[2]Patent: CN105985295,2016,A .Location in patent: Paragraph 0078; 0079.

11
2-(5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-ylthio)acetic acid methyl ester [ No CAS ]
[ 1158970-52-5 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide; In tetrahydrofuran; at 20℃; for 2h;	To a three-necked flask, 4-(4-cyclopropylnaphthalene)-3-methyl thioacetate-5-bromo-1,2,4-triazole (compound 4 without purification in the previous step, 4.93 g, 11.80 mmol) and tetrahydrofuran (10V, 49.30 ml) were added, and IN sodium hydroxide solution (23.60 ml, 23.60 mmol) was slowly added dropwise to the solution at room temperature. The mixture was stirred at room temperature for 2 hours. After the end of the reaction confirmed by LC, the reaction mixture was diluted with water. After the aqueous phase was washed twice with ethyl acetate, it was adjusted to acidity by adding IN hydrochloric acid solution. The aqueous phase was further extracted with ethyl acetate twice. The resulting organic phase was dried and concentrated to dryness to obtain compound 6 as white solid (purity: 98%) in two steps (yield 75%). (0053) 1H NMR (400 MHz, CDCl3) δ 8.57 (d, J=8.4 Hz, 1H), 8.26 (bs, 1H), 7.70-7.66 (m, 1H), 7.62-7.58 (m, 1H), 7.38 (s, 2H), 7.23 (d, J=8.4 Hz, 1H), 4.03 (d, J=15.6 Hz, 1H), 3.96 (d, J=15.6 Hz, 1H), 2.47-2.43 (m, 1H), 1.22-1.17 (m, 2H), 0.91-0.87 (m, 2H); MS (ESI) m/z 404.00 ([M+H]+).

References: [1]Patent: CN105985295,2016,A .
[2]Patent: US2020/62720,2020,A1 .Location in patent: Paragraph 0051-0053.

12
[ 878671-93-3 ]
[ 1158970-52-5 ]

References: [1]Patent: CN105985295,2016,A .

13
[ 878671-94-4 ]
[ 1158970-52-5 ]

References: [1]Patent: CN105985295,2016,A .
[2]Patent: US2020/62720,2020,A1 .
[3]Patent: US2020/62720,2020,A1 .
[4]Patent: US2020/62720,2020,A1 .

14
[ 1158970-52-5 ]
(S)-ethyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate [ No CAS ]
(R)-ethyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 299 - 303.

15
[ 1158970-52-5 ]
(S)-2-((5-bromo-4-(4-cyclopropyl-1-naphthalenyl)-4H-1,2,4-triazol-3-yl)thio)-acetic acid [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 299 - 303.

16
[ 1158970-52-5 ]
(R)-2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetic acid [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2017,vol. 8,p. 299 - 303.

17
ethyl 2-((4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)thio)acetate [ No CAS ]
[ 1158970-52-5 ]

Yield	Reaction Conditions	Operation in experiment
95%	With C20H21BrN3O4S(1+)*Br(1-); In tetrahydrofuran; n-heptane; at 20 - 30℃; for 2h;	The compound VI (R was ethyl, 100.0 g, 282.9 mmol, 1.0 eq.) Was dissolved in 2 L of tetrahydrofuran and stirred at 20 to 30C. The catalyst b5 (2.83 mmol, 1% eq.) Was added successively,N.(70.5 g, 396.1 mmol, 1.4 eq.) For 1.5 hours. To the reaction solution was added 2 L of n-heptane and stirred for 0.5 hour. The filtrate was added with 2 L of saturated sodium bicarbonate solution The organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give a pale yellow compound of formula V (R, ethyl, 116.1 g) in a yield of 95% and a purity of 95.6%.

References: [1]Patent: CN106916115,2017,A .Location in patent: Paragraph 0028; 0029; 0032; 0033; 0036.

18
[ 1158970-52-5 ]
ethyl 2-((5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl)sulfonyl)acetate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
2.32 g	With 3-chloro-benzenecarboperoxoic acid; In dichloromethane; at 20℃; for 4h;	Will be 4.32g ethyl 2 - ((5-bromo-4- (4-cyclopropylnaphthalen-1-yl) -4H-1,2,4-triazol-3-yl) thioacetate) in 250 ml ,Adding 100 ml of methylene chloride, stirring and dissolving, adding 3.80 g of m-chloroperoxybenzoic acid,The reaction was stirred at room temperature for 4 h. To the reaction solution was added 3.16 g of sodium thiosulfate, stirred at room temperature for 30 min,Filtered and concentrated to dryness. The residue was separated on silica gel and eluted with ethyl acetate-n-hexane (1: 3) to give 2.32 g of a pale yellow solid.

References: [1]Patent: CN106831619,2017,A .Location in patent: Paragraph 0015; 0037; 0038.

19
ethyl 2‐((4‐(4‐cyclopropylnaphthalen‐1‐yl)‐5‐hydroxy‐4H‐1,2,4‐triazol‐3‐yl)thio)acetate [ No CAS ]
[ 1158970-52-5 ]

Yield	Reaction Conditions	Operation in experiment
85%	With phosphorus tribromide; In dichloromethane; at 0℃;	(4) 10 g of compound of formula 3 was dissolved in 50 mL of dichloromethane,Add to cool to 0 C,11g of phosphorus tribromide was added dropwise,After dropping the reaction temperature to complete consumption of raw materials;The reaction was cooled to room temperature and poured into 50 mL of water,Points to the water layer,The methylene chloride layer was washed with 1% sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate,Concentrated and dried to give a brown-red oil,Add 120mL absolute ethanol recrystallization 3 times,Obtained white solid powder, dried to give the formula 2Compound 10g,Yield 85%;

References: [1]Patent: CN106866560,2017,A .Location in patent: Paragraph 0046; 0048; 0052.

20
[ 1158970-52-5 ]
2-[5-bromo-4-(4-cyclopropylnaphthalen-1-yl)-4H-1,2,4-triazol-3-yl]sulfanyl}acetic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
96%	With sodium hydroxide; In tetrahydrofuran; at 10 - 15℃;	70 g of the compound of formula 2 was dissolved in 300 mL of tetrahydrofuran,Add 30ml of 10% sodium hydroxide solution,10 ~ 15 reaction to the disappearance of raw materials,The reaction solution was adjusted to pH 1 with 5% hydrochloric acid solution,Add ethyl acetate extraction,After drying over anhydrous magnesium sulfate and concentrating under reduced pressure,Then add acetone recrystallization,Got Lesinurad 60g,The yield is 96%.As shown in Figure 3,The purity of Lesinurad obtained in this example is 99.79%

References: [1]Patent: CN106866560,2017,A .Location in patent: Paragraph 0041; 0047; 0053.

21
C₁₅H₁₃N₃OS [ No CAS ]
[ 1158970-52-5 ]

References: [1]Patent: CN106866560,2017,A .

22
2-((4-cyclopropylnaphthalen-1-yl)carbamothioyl)hydrazine-1-carboxylic acid methyl ester [ No CAS ]
[ 1158970-52-5 ]

References: [1]Patent: CN106866560,2017,A .

23
4-(4-cyclopropylnaphthalene)-3,5-dibromo-1,2,4-triazole [ No CAS ]
[ 1158970-52-5 ]

References: [1]Patent: US2020/62720,2020,A1 .

24
4-(4-cyclopropylnaphthalene)-3,5-dibromo-1,2,4-triazole [ No CAS ]
[ 105-39-5 ]
[ 623-51-8 ]
[ 1158970-52-5 ]

Yield	Reaction Conditions	Operation in experiment
		Example 10 Preparation of 4-(4-cyclopropylnaphthalene)-3-ethyl thioacetate-5-dibromo-1,2,4-triazole To a three-necked flask, 4-(4-cyclopropylnaphthalene)-3,5-dibromo-1,2,4-triazole (compound 3, 4.64 g, 11.80 mmol) and N,N-dimethylformamide (10 V, 46.40 ml) were added, and potassium carbonate (2.45 g, 17.71 mmol) and ethyl mercaptoacetate (2.13 g, 17.71 mmol) were successively added at room temperature. The reaction was stirred at room temperature for 1 hour, and the depletion of the starting material was confirmed by LC. At this time, potassium carbonate (1.79 g, 12.98 mmol) and ethyl chloroacetate (1.59 g, 12.98 mmol) were successively added to the reaction system, and stirring continued for 1 hour at room temperature. After completion of the reaction, the reaction mixture was diluted with ethyl acetate. The organic phase was washed once with 0.5N hydrochloric acid solution, and then washed three times with water. A crude product of compound 19 was obtained by drying and concentrating. It was used for the next reaction without purification (purity 89%, yield 79%). 1H NMR (400 MHz, CDCl3) δ 8.55 (d, J=8.4 Hz, 1H), 7.68-7.64 (m, 1H), 7.60-7.56 (m, 1H), 7.36 (s, 2H), 7.26 (d, J=8.4 Hz, 1H), 4.09 (d, J=16.4 Hz, 1H), 4.03 (d, J=16.4 Hz, 1H), 3.72 (s, 3H), 2.45-2.41 (m, 1H), 1.33-1.27 (t, 3H), 1.19-1.15 (m, 2H), 0.90-0.86 (m, 2H); MS (ESI) m/z 432.03 ([M+H]+).

References: [1]Patent: US2020/62720,2020,A1 .Location in patent: Paragraph 0048-0050.

25
4-(4-cyclopropylnaphthalene)-1,2,4-triazole [ No CAS ]
[ 1158970-52-5 ]

References: [1]Patent: US2020/62720,2020,A1 .
[2]Patent: US2020/62720,2020,A1 .
[3]Patent: US2020/62720,2020,A1 .

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Technical Information

• Benzylic Oxidation • Birch Reduction • Blanc Chloromethylation • Friedel-Crafts Reaction • Hydrogenolysis of Benzyl Ether • Preparation of Alkylbenzene • Reactions of Benzene and Substituted Benzenes • Vilsmeier-Haack Reaction

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H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 1158970-52-5

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CAS No.: 1158970-52-5

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[ 1158970-52-5 ] Synthesis Path-Downstream 1~25

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