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[ CAS No. 1533519-85-5 ]

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Chemical Structure| 1533519-85-5
Chemical Structure| 1533519-85-5
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CAS No. :1533519-85-5 MDL No. :MFCD28404620
Formula : C18H17N3O2S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :339.41 g/mol Pubchem ID :72720796
Synonyms :

Safety of [ 1533519-85-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1533519-85-5 ]

  • Upstream synthesis route of [ 1533519-85-5 ]
  • Downstream synthetic route of [ 1533519-85-5 ]

[ 1533519-85-5 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 1533519-85-5 ]
  • [ 1151516-14-1 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: CN105399694, 2016, A,
[3] Patent: CN105985295, 2016, A,
[4] Patent: CN107098866, 2017, A,
  • 2
  • [ 1533519-84-4 ]
  • [ 96-32-2 ]
  • [ 1533519-85-5 ]
YieldReaction ConditionsOperation in experiment
99.5% With potassium carbonate In N,N-dimethyl-formamide at 25℃; for 3 h; In a 100 ml three-necked flask equipped with a stirrer and a thermometer, 25 ml of DMF was added, the intermediate (III)2.67 g, stirred at room temperature, 1.45 g of potassium carbonate was added, and 1.61 g of methyl bromoacetate was added dropwise at 25 ° C,Stirring was continued for 3 hours; 50 ml of water was added and extracted with ethyl acetate 50 ml x3 to combine the organic phase,The ethyl acetate was concentrated and concentrated, and 50 ml of methanol was added thereto. The crystals were recrystallized, filtered and dried to give 3.22 g of product,Namely intermediate (IV), yield 99.5percent.
4 g With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5 h; The reaction flask was added to 250mL of 4- (4-cyclopropyl-naphthalen-1-yl) -4H-1,2,4- triazole-3-thiol (compound A, 5g,0.018mol), potassium carbonate (3.74g, 0.027mol, 1.5eq), DMF (50ml). Stirring solution of ethyl bromoacetate (3.3g,0.022mol, 1.2eq). Dropping was completed, the reaction was stirred room temperature for 1.5h. Sample testing of raw materials after completion of the reaction, to the reaction mixture was stirred atWas added dropwise in ice water 100ml, white solid was precipitated. Stirring 30min, filtration, washing with water. After drying the filter cake with acetic acidRecrystallized from ethyl to give a white solid 4g, i.e. intermediates B.
4 g With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 1.5 h; To a 250 mL reaction flask was added 4-(4-cyclopropylnaphthalen-1-yl)-4Η-1,2,4-triazole-3-thiol (Compound A, 58, 0.01811101), potassium carbonate (3.748, 0.02711101, 1.569), 01 ^ (5011 ^). Ethyl bromoacetate was added dropwise with stirring (3.3 g, 0.022 mol 1,1.2 eq). After completion of the reaction, the reaction was stirred at room temperature for 1.5 h. Sampling After testing the raw material, the reaction is complete, Should be added to the liquid ice water 1OOmL, a white solid precipitation. Stir for 30min, suction filter, washed. After the cake was dried, the residue was washed with ethyl acetate Recrystallization gave
Reference: [1] Patent: CN105906576, 2016, A, . Location in patent: Paragraph 0070; 0071; 0083; 0084
[2] Patent: WO2014/8295, 2014, A1, . Location in patent: Paragraph 0254-0262
[3] Patent: CN105399694, 2016, A, . Location in patent: Paragraph 0085; 0086; 0087; 0088
[4] Patent: CN107098866, 2017, A, . Location in patent: Paragraph 0079; 0080; 0081; 0082; 0083
  • 3
  • [ 1533519-84-4 ]
  • [ 1533519-85-5 ]
YieldReaction ConditionsOperation in experiment
90% With potassium phosphate In water; acetone at 40℃; for 6 h; Example 8. Preparation of methyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate [073] To a round bottom flask added 4-(4-cyclopropyl-l-yl)-4H-l, 2,4-triazole-3-thiophenol (54.0 g), acetone/water (500 mL/25 mL), methyl chloroacetate (17.8 mL) and potassium carbonate (33.5 g) to form a mixture, the mixture was heated to about 40°C, after stirred for about 6 hours, the mixture was cooled to room temperature (about 19°C), then was added water (about 400 mL), stirred for about 5 minutes followed by removing acetone, filtered, the filter cake was washed with water and dried in vacuum at about 50°C for about 12 hours to obtain methyl 2-((4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazol-3-yl)thio)acetate 65.0 g, yield 90percent. LC-Ms: m/z (ESI): 402 (M+H)+, 1H MR (400 MHz, CDC13): δ 8.54 (d, J=8.0 Hz, 1 H), 8.32 (s, 1 H), 7.66 (m, 1 H), 7.54 (m, 1 H), 7.34-7.41 (m, 5 H), 7.23 (m, 1 H), 7.10 (m, 2H), 4.30 (dd, J=8.0, 12 Hz, 2 H), 2.43 (m, 1 H), 1.17 (m, 2 H), 0.86 (m, 2 H).
Reference: [1] Patent: WO2014/198241, 2014, A1, . Location in patent: Paragraph 072-073
  • 4
  • [ 127971-24-8 ]
  • [ 24127-59-1 ]
  • [ 1533519-85-5 ]
YieldReaction ConditionsOperation in experiment
93.8% With potassium carbonate In N,N-dimethyl-formamide at 50℃; for 2.5 h; 3) 17.3 g (0.1 mol) of the intermediate methyl 2- (4H-1,2,4-triazole-3-mercapto) acetate was dissolved in 170 ml of DMF,24.8 g of 1-cyclopropyl-4-bromonaphthalene and 13.8 g of potassium carbonate were heated to 50 ° C and the reaction was stirred for about 2.5 hours.Then, the crystals were filtered off and the cake was washed once with ethyl acetate (n-hexane = 1: 2)And then dried in a vacuum oven at 50 ° C for 7 hours. To obtain the target intermediate2 - ((4- (4-cyclopropylnaphthalen-1-yl) 4-H-1,2,4-triazole-3-yl) thio) acetate31.8 g,The yield was about 93.8percent, HPLC purity: 99.8percent.
Reference: [1] Patent: CN106187927, 2016, A, . Location in patent: Paragraph 0030
  • 5
  • [ 24127-59-1 ]
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YieldReaction ConditionsOperation in experiment
82% With pyridine; copper dichloride In tetrahydrofuran at 20℃; 34 g of 2-(4-cyclopropyl-1-naphthyl)-4,4,5,5-tetramethyl-1,3-dioxaborolane was placed in a 10L beaker and 1 L of tetrahydrofuran solution was added. With stirring and dissolution, 15 g of cupric chloride, 36 g of (4H-1,2,4-triazol-3-ylmercapto)acetate and 30 mL of pyridine were added successively.The mixture was stirred at room temperature overnight. The resulting reaction solution was diluted with 2 L of dichloromethane, washed with 2 L of saturated saline, and the organic phase was collected and dried over anhydrous sodium sulfate, concentrated under reduced pressure, and filtered.Obtained methyl 2-(4-(4-cyclopropyl-1-naphthyl)-4hydro-1,2,4triazol-3-ylsulfanyl)acetate 32g, yield 82percent; purity 98.1 percent. .
Reference: [1] Patent: CN107955029, 2018, A, . Location in patent: Paragraph 0058-0060; 0074-0076; 0090-0092
  • 6
  • [ 878671-94-4 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/198241, 2014, A1,
[4] Patent: CN105985295, 2016, A,
  • 7
  • [ 25033-19-6 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
[4] Patent: CN105985295, 2016, A,
  • 8
  • [ 878671-93-3 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
[4] Patent: CN105985295, 2016, A,
  • 9
  • [ 878671-95-5 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/198241, 2014, A1,
[3] Patent: CN105985295, 2016, A,
  • 10
  • [ 1533519-86-6 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/198241, 2014, A1,
[3] Patent: CN105985295, 2016, A,
  • 11
  • [ 90-11-9 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
  • 12
  • [ 1533519-87-7 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
  • 13
  • [ 1533519-92-4 ]
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Reference: [1] Patent: WO2014/8295, 2014, A1,
  • 14
  • [ 1533519-91-3 ]
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Reference: [1] Patent: WO2014/8295, 2014, A1,
  • 15
  • [ 2298-07-9 ]
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Reference: [1] Patent: WO2014/198241, 2014, A1,
  • 16
  • [ 571-57-3 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: CN105906576, 2016, A,
  • 17
  • [ 127971-24-8 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: CN107955029, 2018, A,
  • 18
  • [ 83-53-4 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: CN107955029, 2018, A,
  • 19
  • [ 96-32-2 ]
  • [ 1533519-85-5 ]
Reference: [1] Patent: CN105985295, 2016, A, . Location in patent: Paragraph 0045; 0046; 0047
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