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[ CAS No. 1533519-84-4 ] {[proInfo.proName]}

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Chemical Structure| 1533519-84-4
Chemical Structure| 1533519-84-4
Structure of 1533519-84-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1533519-84-4 ]

CAS No. :1533519-84-4 MDL No. :MFCD28404707
Formula : C15H13N3S Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W :267.35 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 1533519-84-4 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.2
Num. rotatable bonds : 2
Num. H-bond acceptors : 1.0
Num. H-bond donors : 1.0
Molar Refractivity : 78.72
TPSA : 65.7 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : Yes
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : No
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -5.3 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.58
Log Po/w (XLOGP3) : 3.71
Log Po/w (WLOGP) : 3.9
Log Po/w (MLOGP) : 2.65
Log Po/w (SILICOS-IT) : 4.49
Consensus Log Po/w : 3.46

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.29
Solubility : 0.0138 mg/ml ; 0.0000516 mol/l
Class : Moderately soluble
Log S (Ali) : -4.78
Solubility : 0.00443 mg/ml ; 0.0000166 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -4.94
Solubility : 0.00306 mg/ml ; 0.0000115 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.89

Safety of [ 1533519-84-4 ]

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 [ 1533519-84-4 ]

* 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 [ 1533519-84-4 ]
  • Downstream synthetic route of [ 1533519-84-4 ]

[ 1533519-84-4 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 1533519-84-4 ]
  • [ 1151516-14-1 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: CN105399694, 2016, A,
[3] Patent: CN105906576, 2016, A,
[4] Patent: CN107098866, 2017, A,
  • 2
  • [ 1533519-86-6 ]
  • [ 1533519-84-4 ]
YieldReaction ConditionsOperation in experiment
90% With water; sodium hydroxide In N,N-dimethyl-formamide at 30℃; for 16 h; Example 5. Preparation of 4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazole-3-thiol [070] To a round bottom flask added 4-(4-cyclopropyl-naphthalen-l-yl) -1-formylamino-thiourea (64.0 g, 225 mmol), DMF (300 mL) and 1 mol/L aqueous sodium hydroxide solution (225 mL) to form a mixture, the mixture was heated to about 30°C after stirred for about 16 hours, the mixture was cooled to room temperature (about 20°C). 1 mol/L hydrochloric acid (about 200 mL) was added into the mixture until the pH value of the mixture was about 6.0, then water (about 500 mL) was added. The mixture was stirred for about 15 minutes and filtered. The filter cake was washed with water, and the product was dried in vacuum at about 50°C for about 5 hours to obtain gray-green solid 4-(4-cyclopropylnaphthalen-l-yl)-4H-l,2,4-triazole-3 -thiol, 54.0 g, yield 90percent. LC-Ms: m/z (ESI): 268(M+H)+, 1H MR (400 MHz, acetone-d6): δ 8.57 (d, J=8.0 Hz, 1 H), 8.37 (s, 1 H), 7.67 (m, 1 H), 7.60(m, 1 H), 7.5 l(d, J=8.0 Hz, 1 H), 7.48 (d, J=8.0 Hz, 1 H), 7.43 (d, J=8.0 Hz, 1 H), 2.50 (m, 1 H), 1.16 (m, 2 H), 0.84 (m, 2 H).
Reference: [1] Patent: WO2014/198241, 2014, A1, . Location in patent: Paragraph 069-070
[2] Patent: WO2014/8295, 2014, A1, . Location in patent: Paragraph 0337
  • 3
  • [ 23719-80-4 ]
  • [ 1533519-84-4 ]
YieldReaction ConditionsOperation in experiment
89.89% for 2 h; In a 100 ml three-necked flask equipped with a stirrer and a thermometer, 50 ml of tetrahydrofuran was added, and the intermediate(II) 2.62 g, 30 ml of 0.5 mol / L cyclopropylmagnesium bromide / THF solution was added;Add, stir for 2 hours, add saturated ammonium chloride quenching, filtration, the filtrate concentrated to remove THF, then add dichloromethane 25mlAnd the mixture was concentrated twice to give dichloromethane to give 2.4 g of product, i.e., intermediate (III), and the yield89.89percent.
Reference: [1] Patent: CN105906576, 2016, A, . Location in patent: Paragraph 0068; 0069; 0081; 0082
  • 4
  • [ 878671-94-4 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/198241, 2014, A1,
  • 5
  • [ 90-11-9 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
  • 6
  • [ 25033-19-6 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
  • 7
  • [ 878671-93-3 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/8295, 2014, A1,
[3] Patent: WO2014/8295, 2014, A1,
  • 8
  • [ 878671-95-5 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
[2] Patent: WO2014/198241, 2014, A1,
  • 9
  • [ 1533519-87-7 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
  • 10
  • [ 1533519-92-4 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
  • 11
  • [ 1533519-91-3 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/8295, 2014, A1,
  • 12
  • [ 2298-07-9 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: WO2014/198241, 2014, A1,
  • 13
  • [ 571-57-3 ]
  • [ 1533519-84-4 ]
Reference: [1] Patent: CN105906576, 2016, A,
  • 14
  • [ 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
  • 15
  • [ 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
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