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[ CAS No. 939-69-5 ] {[proInfo.proName]}

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Chemical Structure| 939-69-5
Chemical Structure| 939-69-5
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Product Details of [ 939-69-5 ]

CAS No. :939-69-5 MDL No. :MFCD00296905
Formula : C8H4N2OS Boiling Point : -
Linear Structure Formula :- InChI Key :SQAVNBZDECKYOT-UHFFFAOYSA-N
M.W : 176.20 Pubchem ID :9881912
Synonyms :

Calculated chemistry of [ 939-69-5 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 9
Fraction Csp3 : 0.0
Num. rotatable bonds : 0
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 46.36
TPSA : 85.15 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.76 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.43
Log Po/w (XLOGP3) : 2.28
Log Po/w (WLOGP) : 1.87
Log Po/w (MLOGP) : 0.22
Log Po/w (SILICOS-IT) : 2.6
Consensus Log Po/w : 1.68

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.92
Solubility : 0.21 mg/ml ; 0.00119 mol/l
Class : Soluble
Log S (Ali) : -3.71
Solubility : 0.0347 mg/ml ; 0.000197 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.48
Solubility : 0.586 mg/ml ; 0.00333 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 939-69-5 ]

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

Application In Synthesis of [ 939-69-5 ]

* 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.

  • Upstream synthesis route of [ 939-69-5 ]
  • Downstream synthetic route of [ 939-69-5 ]

[ 939-69-5 ] Synthesis Path-Upstream   1~20

  • 1
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YieldReaction ConditionsOperation in experiment
99% at 200℃; Pyridine hydrochloride (2.32 g) was added to 2-cyano-6-methoxybenzothiazole 31 (51.4 mg, 0.271 mmol) and heated to 200°C in an argon atmosphere to dissolve the pyridine hydrochloride, and the reaction mixture was stirred for 30 minutes.
The reaction mixture was allowed to cool, and then 1 M hydrochloric acid (50 ml) was added.
After extraction with ethyl acetate (3 x 50 ml) and drying of the organic layer with anhydrous sodium sulfate, the result was concentrated in vacuo.
The resulting residue was purified by preparative thin-layer silica gel chromatography {one 20 cm x 20 cm x 1.75 mm plate; hexane-ethyl acetate (1:1)}, yielding 2-cyano-6-hydroxybenzothiazole 32 (47.2 mg, 99percent) as a pale yellow solid.
1H NMR (270 MHz, CD3OD) δ 7.17 (1H, dd, J = 2.7, 9.2 Hz), 7.41 (1H, d, J = 2.7 Hz), 7.99 (1H, d, J = 9.2 Hz)
89% at 200℃; for 1 h; Inert atmosphere Pyridinium chloride (19.5 g) was added to 6-methoxybenzo [d] thiazole-2-carbonitrile (766 mg, 4.03 mmol) under argon atmosphere at room temperature. The obtained mixture was heated to 200 ° C. under an argon atmosphere to melt the pyridinium chloride and then stirred at 200 ° C. for 1 hour.The reaction mixture was allowed to cool to room temperature, 2 M hydrochloric acid (250 mL) was added, and the mixture was further extracted with ethyl acetate (3 × 100 mL). The combined organic layer was dried over anhydrous sodium sulfate, and then the solvent was distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (silica gel 85 g; hexane-ethyl acetate (1: 1)) to give 6-hydroxybenzo [d] thiazole-2-carbonitrile
88% at 200℃; for 0.666667 h; Inert atmosphere; Microwave irradiation 2-Cyano-6-hydroxybenzothiazole; Compound 1 was synthesized using a method modified from the literature (Yao H S, Min-kyung; Rao, Jianghong (2007) A bioluminogenic Substrate for In Vivo Imaging of beta-Lactamase Activity. Angew Chem Int Ed 46:7031-7034). Pyridine hydrochloride (1.0 g, 8.65 mmol) and 2-cyano-6-methoxybenzothiazole, Compound 2, (0.5 g, 2.63 mmol) were added to a 5 mL microwave flask with a stirbar. Nitrogen gas (N2) was added to the reaction vessel immediately before it was shut. The flask was heated to 200° C. using a power level of 150 W for 40 minutes in a Biotage microwave synthesizer. The reaction was stirred at 600 rpm. The reaction mixture was cooled and neutralized with sodium bicarbonate. During neutralization, the crude product precipitated from the solution as a yellow solid. The precipitate was filtered, and the filtrate was washed three times with ethyl acetate (EtOAc). Combination of the crude product from the EtOAc washes and the yellow precipitate and purification on a silica column (70:30 hexanes:EtOAc, dry loaded) yielded 408.7 mg (88percent) of the pure product. 1H NMR (300 MHz, CD3OD): δ 7.13 (1H, dd, J=9 Hz), 7.36 (1H, d, J=2.1 Hz), 7.95 (1H, d, J=9 Hz). LRESI-MS: calculated for [C8H4N2OS] 176.0. found 176.1.
88% at 200℃; for 0.666667 h; Inert atmosphere; Microwave irradiation Pyridine hydrochloride (1.0 g, 8.65 mmol) and 2-cyano-6-methoxybenzothiazole, 2, (0.5 g, 2.63 mmol) were added to a 5 mL microwave flask with a stirbar.
Nitrogen gas was added to the reaction vessel immediately before it was shut.
The flask was heated to 200° C. using a power level of 150 W for 40 minutes in a Biotage microwave synthesizer.
The reaction was stirred at 600 rpm.
The reaction was cooled and neutralized with sodium bicarbonate.
During neutralization, the crude product precipitated from the solution as a yellow solid.
The precipitate was filtered, and the filtrate was washed three times with ethyl acetate.
Combination of the crude product from the ethyl acetate washes and the yellow precipitate and purification on a silica column (70:30 hexanes:ethyl acetate, dry loaded) yielded 408.7 mg (88percent) of the pure product. 1H NMR (300 MHz, CD3OD): δ 7.13 (1H, dd, J=9 Hz), 7.36 (1H, d, J=2.1 Hz), 7.95 (1H, d, J=9 Hz). LRESI-MS: calculated for [C8H4N2OS] 176.0. found 176.1.
83% With chloro-trimethyl-silane; ethanethiol; potassium iodide In acetonitrile at -5 - 30℃; for 6 h; In 500 ml is provided with a thermometer, dropping funnel, stirrer, drying tube in the four-port flask, add 150 ml acetonitrile, 2-cyano-6-methoxybenzothiazole 20g (105.14mmol), potassium iodide 26.18g (157.71mmol) stirring dissolved, add 0.65g (10.51mmol) ethyl mercaptan at -5 °C lower dropwise chlorotrimethylsilane 17.13g (157.71mmol) acetonitrile solution, after dripping, raising the temperature to 30 °C reaction 6 hours, after the reaction, quenching reaction adds by drops full and sodium carbonate aqueous solution, adjusted to pH 9, by adding ethyl acetate 100 ml extraction 3 time, combined with the phase, then using 100 ml water backwash organic phase 3 time, combined with the phase, drying, removing dissolved product 1 (15.38g, 83percent).
70% at 210℃; for 0.5 h; Inert atmosphere General procedure: The methoxycarbonitrile derivative (1 eq) was mixed with pyridinium chloride (5 eq) under argon and heated to 210°C for 30 minutes. The resulting mixture was partitioned between distilled water and dicloromethane, and the organic layers were concentrated under vacuum. The crude product was dissolved in 5 percent Na2CO3 (50 ml) and filtered before addition of HCl until pH ≈4.0. The aqueous layer was extracted with dichloromethane (50 mL) and the organic layers removed under vacuum yielding pure product (>98percent).

Reference: [1] Patent: EP2754657, 2014, A1, . Location in patent: Paragraph 0088-0090
[2] Patent: US5616729, 1997, A,
[3] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
[4] Chemistry - A European Journal, 2016, vol. 22, # 27, p. 9330 - 9337
[5] Patent: JP6095208, 2017, B2, . Location in patent: Paragraph 0048-0050
[6] Journal of the American Chemical Society, 2013, vol. 135, # 5, p. 1783 - 1795
[7] Patent: US2013/287699, 2013, A1, . Location in patent: Paragraph 0416
[8] Patent: US2013/315829, 2013, A1, . Location in patent: Paragraph 0188
[9] Angewandte Chemie - International Edition, 2007, vol. 46, # 37, p. 7031 - 7034
[10] Patent: CN105384704, 2016, A, . Location in patent: Paragraph 0046; 0047
[11] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 2, p. 392 - 395
[12] Chemical Communications, 2018, vol. 54, # 14, p. 1774 - 1777
[13] Bioconjugate Chemistry, 2012, vol. 23, # 9, p. 1902 - 1908,7
[14] Bioconjugate Chemistry, 2012, vol. 23, # 9, p. 1902 - 1908
[15] European Journal of Medicinal Chemistry, 2015, vol. 94, p. 140 - 148
[16] Chemical Communications, 2009, # 27, p. 4028 - 4030
[17] Journal of the American Chemical Society, 2010, vol. 132, # 25, p. 8563 - 8565
[18] Journal of the American Chemical Society, 2012, vol. 134, # 18, p. 7604 - 7607
[19] Journal of the American Chemical Society, 1963, vol. 85, p. 337 - 343
  • 2
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YieldReaction ConditionsOperation in experiment
42% With trimethylsilyl iodide In diethyl ether; chloroform; dimethyl sulfoxide EXAMPLE 6
2-Cyano-6-hydroxybenzothiazole (Variant 3) STR10
3 g. (0.015 mol) 2-Chloro-6-methoxybenzothiazole are dissolved in 9 ml. anhydrous chloroform and mixed with 6 g. (4.5 ml.) (0.03 mol) iodotrimethylsilane.
The solution is stirred under reflux at a bath temperature of 80° C.
After 25 hours, a further 3 g. (2.1 ml.) iodotrimethylsilane are added thereto and the reaction mixture stirred under reflux.
After a further reaction period of 30 hours, the solution is evaporated in a vacuum.
The residue is dissolved in 100 ml. dimethyl sulphoxide and mixed with 3 g. potassium cyanide (the three fold molar amount).
The suspension is then stirred at 100° C.
After a reaction period of 3 hours, the reaction mixture is poured into about 800 ml. ice-water, acidified with 2N hydrochloric acid, extracted once with 500 ml. and once with 300 ml. of diethyl ether.
The combined extracts are washed with water, dried with anhydrous sodium sulphate and evaporated.
The still slightly contaminated product is purified over silica gel 60 with diisopropyl ether-tetrahydrofuran (4:1 v/v).
The yield is 42percent of theory.
Reference: [1] Patent: US4826989, 1989, A,
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Reference: [1] Synlett, 2009, # 16, p. 2682 - 2684
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
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Reference: [1] Journal of the American Chemical Society, 1963, vol. 85, p. 337 - 343
[2] Journal of the American Chemical Society, 1963, vol. 85, p. 337 - 343
  • 7
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Reference: [1] Journal of the American Chemical Society, 1963, vol. 85, p. 337 - 343
[2] Journal of the American Chemical Society, 1963, vol. 85, p. 337 - 343
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Reference: [1] Journal of the American Chemical Society, 1963, vol. 85, p. 337 - 343
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Reference: [1] Journal of the American Chemical Society, 1963, vol. 85, p. 337 - 343
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Reference: [1] Journal of the American Chemical Society, 1963, vol. 85, p. 337 - 343
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 18, p. 7604 - 7607
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
[3] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
[4] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
[5] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
  • 12
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Reference: [1] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 2, p. 392 - 395
[2] Patent: US4826989, 1989, A,
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Reference: [1] Journal of the American Chemical Society, 1963, vol. 85, p. 337 - 343
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 18, p. 7604 - 7607
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
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Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 18, p. 7604 - 7607
[2] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
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Reference: [1] Turkish Journal of Chemistry, 2018, vol. 42, # 6, p. 1499 - 1517
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Reference: [1] Turkish Journal of Chemistry, 2018, vol. 42, # 6, p. 1499 - 1517
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Reference: [1] Journal of the American Chemical Society, 2013, vol. 135, # 5, p. 1783 - 1795
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 7, p. 2117 - 2121
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