939-69-5|6-Hydroxybenzo[d]thiazole-2-carbonitrile| Ambeed

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Quality Control of [ 939-69-5 ] Purity: 97% SDS Specification

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Product Details of [ 939-69-5 ]

CAS No. :	939-69-5
Formula :	C₈H₄N₂OS
M.W :	176.20
SMILES Code :	N#CC1=NC2=CC=C(O)C=C2S1
MDL No. :	MFCD00296905
InChI Key :	SQAVNBZDECKYOT-UHFFFAOYSA-N
Pubchem ID :	9881912

Safety of [ 939-69-5 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H319
Precautionary Statements:	P305+P351+P338

Computational Chemistry of [ 939-69-5 ] Show Less

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 ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	85.15 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.43
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	2.28
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.87
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	0.22
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	2.6
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.68

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.92
Solubility	0.21 mg/ml ; 0.00119 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.71
Solubility	0.0347 mg/ml ; 0.000197 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-2.48
Solubility	0.586 mg/ml ; 0.00333 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	No
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.76 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	2.22

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.

Downstream synthetic route of [ 939-69-5 ]

[ 939-69-5 ] Synthesis Path-Downstream 1~35

1
[ 108-24-7 ]
[ 939-69-5 ]
[ 38292-82-9 ]

References: [1]Tetrahedron,1972,vol. 28,p. 4075 - 4082.

2
[ 623-51-8 ]
[ 939-69-5 ]
[ 37657-63-9 ]

References: [1]Tetrahedron,1972,vol. 28,p. 4065 - 4074.

3
[ 60-23-1 ]
[ 939-69-5 ]
[ 2590-08-1 ]

References: [1]Journal of Organic Chemistry,1965,vol. 30,p. 2344 - 2348.

4
[ 91634-13-8 ]
[ 939-69-5 ]

References: [1]Journal of the American Chemical Society,1963,vol. 85,p. 337 - 343.

5
[ 19788-49-9 ]
[ 939-69-5 ]
[ 37657-62-8 ]

References: [1]Tetrahedron,1972,vol. 28,p. 4065 - 4074.
[2]Journal of the American Chemical Society,2009,vol. 131,p. 11590 - 11605.

6
[ 33441-50-8 ]
[ 939-69-5 ]
[ 37657-61-7 ]

References: [1]Tetrahedron,1972,vol. 28,p. 4065 - 4074.

7
[ 921-01-7 ]
[ 939-69-5 ]
[ 20240-21-5 ]

References: [1]Journal of the American Chemical Society,1963,vol. 85,p. 337 - 343.

8
[ 52-90-4 ]
[ 939-69-5 ]
[ 34500-31-7 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate; In water; at 20℃; for 3h;	General procedure: The hydroxy- or methoxycarbonitrile derivative (1 eq) was added to the cysteine derivative (1.05 eq) and sodium carbonate (3 eq) in 5 ml water. The mixture was stirred at room temperature for three hours before addition of dilute HCl (1 M) to pH ? 3.5 ? 4.0. The product was isolated by extraction with diethyl ether, washed by water, followed by evaporation

References: [1]Journal of the American Chemical Society,1963,vol. 85,p. 337 - 343.
[2]Chemical Communications,2015,vol. 51,p. 5425 - 5428.
[3]European Journal of Medicinal Chemistry,2015,vol. 94,p. 140 - 148.

9
[ 349-46-2 ]
[ 939-69-5 ]
[ 2591-17-5 ]

References: [1]Journal of the American Chemical Society,1963,vol. 85,p. 337 - 343.

10
[ 2935-90-2 ]
[ 939-69-5 ]
[ 66069-76-9 ]

References: [1]Journal of Organic Chemistry,1978,vol. 43,p. 2366 - 2369.

11
[ 98429-31-3 ]
[ 939-69-5 ]
[ 37657-61-7 ]

References: [1]Journal of the American Chemical Society,1967,vol. 89,p. 7148 - 7150.

12
[ 52-66-4 ]
[ 939-69-5 ]
[ 895-58-9 ]

References: [1]Journal of Organic Chemistry,1965,vol. 30,p. 2344 - 2348.

13
[ 52-89-1 ]
[ 939-69-5 ]
[ 37657-66-2 ]

References: [1]Tetrahedron,1972,vol. 28,p. 4065 - 4074.

14
[ 52-89-1 ]
[ 939-69-5 ]
[ 20240-21-5 ]

References: [1]Tetrahedron,1972,vol. 28,p. 4065 - 4074.

15
[ 943-03-3 ]
[ 939-69-5 ]

Yield	Reaction Conditions	Operation in experiment
99%	With pyridine hydrochloride; 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) delta 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)
95%	In methanol; hexane; ethyl acetate;	STR24 2-Cyano-6-hydroxybenzothiazole. Dry pyridinium hydrochloride (34.0 g, 0.294 mol) and 2-cyano-6-methoxy-benzothiazole (Aldrich Chemical Co., 3.0 g, 0.016 mol) were added into a 500 mL round bottom flask which was preheated in an oil bath at 100° C. The bath temperature was increased to 190° C. and the reaction mixture was refluxed at this temperature for 2 h. After the completion of reaction, it was cooled to room temperature to obtain a yellow solid which was dissolved in methanol. Silica was added to this solution and evaporated to dryness. This material was then chromatographed using 30percent ethyl acetate/hexane to obtain 2.7 g of the product as a white solid (95percent): mp 120° C.; 1 H NMR (CD3 OD) delta 5.68 (bs, 1H), 8.02-8.82 (m, 3H); -- C NMR (CD3 OD) delta 106.96, 114.26, 119.59, 126.53, 133.83, 138.93, 147.25, 160.23; MS m/e (rel intensity) 176 (100), 151 (3), 124 (5), 96 (15), 85 (4), 69 (7), 57 (5); Exact mass: calcd 176.0044, found 176.0047. STR25
89%	With pyridine hydrochloride; at 200℃; for 1h;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%	With pyridine hydrochloride; at 200℃; for 0.666667h;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): delta 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%	With pyridine hydrochloride; at 200℃; for 0.666667h;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): delta 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 6h;	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%	With pyridine hydrochloride; at 210℃; for 0.5h;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).
54%	With pyridine hydrochloride; at 200℃; for 2h;	Pyridine hydrochloride (1.8 g, 15.57 mmol) was added to a 15 mL pressure tube and heated to 200 °C until completely dissolved.Then 2-cyano-6-methoxybenzothiazole (100 mg, 0.53 mmol) was added, followed by a reaction at 200 ° C for 2 h.The above reaction solution was adjusted to pH 7 with a 10percent NaHCO3 solution under ice bath. With EtOAc (15mL × 5) mixture was extracted, the organic layer was dried over anhydrous Na2SO4 and concentrated, the solvent was removed under reduced pressure.The crude product was purified by silica gel column chromatography (silica, hexane:EtOAc, 8:1 v/v).Obtained 50 mg of a white solid.The yield was 54.0percent.
	With pyridine hydrochloride; at 180℃; for 1h;Sealed tube; Inert atmosphere;	Pyridine hydrochloride (1.18 g, 10.2 mmol, 10 eq) and 6-methoxy-2-cyanobenzothiazole (0.195 g, 1 .02 mmol, 1 eq) were combined in a rigorously dried sealed tube, purged and placed underan inert nitrogen atmosphere. The reaction mixture was then stirred at 180 00 for 1 h. The resulting red-brown residue was cooled to room temperature and then dissolved in EtOAc (20 mL) and washed with saturated NaHCO3 (1 x 20 mL), 1M HCI (1 x 10 mL), H20 (4 x 10 mL), and brine (1 x 1 0 mL). The organic layer was dried over MgSO4, filtered, and concentrated in vacuo. The crude product was purified using column chromatography eluting with 3:7 EtOAc:Hexane to yield 2-cyano-6-hydroxybenzothiazole as a pale yellow solid. Mp: 202-207 0C (lit. 205-207 oc). 1H-NMR(400 MHz, DMSO) 510.51 (1H, brs, -OH), 7.89 (1H, d, J = 9.0 Hz, H-4), 7.60 (1H, d, J = 2.4 Hz,H-7), 7.19 (1H, dd, J = 9.1, 2.4 Hz, H-5) ppm. 13C-NMR (100.6 MHz, CDCI3) 5160.4(0-2), 147.4(C-6), 139.1 (C-3), 134.0 (0-8), 126.8 (C-7), 119.8 (C-5), 114.4 (C-i), 107.5 (C-4) ppm. MS(ESI+): m/z Calculated for C8H4N2OS [M+H] 177.0122, found 177.0117.

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[7]Patent: US2013/287699,2013,A1 .Location in patent: Paragraph 0416.
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[10]Patent: CN105384704,2016,A .Location in patent: Paragraph 0046; 0047.
[11]Bulletin of the Chemical Society of Japan,1992,vol. 65,p. 392 - 395.
[12]Chemical Communications,2018,vol. 54,p. 1774 - 1777.
[13]Bioconjugate Chemistry,2012,vol. 23,p. 1902 - 1908,7.
[14]European Journal of Medicinal Chemistry,2015,vol. 94,p. 140 - 148.
[15]Chemical Communications,2009,p. 4028 - 4030.
[16]Journal of the American Chemical Society,2010,vol. 132,p. 8563 - 8565.
[17]Journal of the American Chemical Society,2012,vol. 134,p. 7604 - 7607.
[18]Patent: CN109293653,2019,A .Location in patent: Paragraph 0107-0108.
[19]Journal of the American Chemical Society,1963,vol. 85,p. 337 - 343.
[20]Patent: WO2019/21202,2019,A1 .Location in patent: Page/Page column 27.

16
[ 79-03-8 ]
[ 939-69-5 ]
2-cyano-6-(propionyloxy)benzothiazole [ No CAS ]