[ CAS No. 90418-93-2 ] {[proInfo.proName]}

Name: 90418-93-2|2-Methylbenzo[d]thiazole-5-carbonitrile|97%
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SKU: A127333
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Quality Control of [ 90418-93-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 90418-93-2 ]

SDS Specification

Alternatived Products of [ 90418-93-2 ]

Product Details of [ 90418-93-2 ]

CAS No. :	90418-93-2	MDL No. :	MFCD18415973
Formula :	C₉H₆N₂S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	LMGBAGZYSFICDQ-UHFFFAOYSA-N
M.W :	174.22	Pubchem ID :	15089712
Synonyms :

Calculated chemistry of [ 90418-93-2 ]

Physicochemical Properties

Num. heavy atoms :	12
Num. arom. heavy atoms :	9
Fraction Csp3 :	0.11
Num. rotatable bonds :	0
Num. H-bond acceptors :	2.0
Num. H-bond donors :	0.0
Molar Refractivity :	49.3
TPSA :	64.92 Å²

Pharmacokinetics

GI absorption :	High
BBB permeant :	Yes
P-gp substrate :	No
CYP1A2 inhibitor :	Yes
CYP2C19 inhibitor :	No
CYP2C9 inhibitor :	No
CYP2D6 inhibitor :	No
CYP3A4 inhibitor :	No
Log Kp (skin permeation) :	-5.59 cm/s

Lipophilicity

Log Po/w (iLOGP) :	2.06
Log Po/w (XLOGP3) :	2.5
Log Po/w (WLOGP) :	2.48
Log Po/w (MLOGP) :	1.15
Log Po/w (SILICOS-IT) :	3.54
Consensus Log Po/w :	2.35

Druglikeness

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

Water Solubility

Log S (ESOL) :	-3.05
Solubility :	0.155 mg/ml ; 0.000891 mol/l
Class :	Soluble
Log S (Ali) :	-3.51
Solubility :	0.054 mg/ml ; 0.00031 mol/l
Class :	Soluble
Log S (SILICOS-IT) :	-3.44
Solubility :	0.0634 mg/ml ; 0.000364 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	0.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	2.11

Safety of [ 90418-93-2 ]

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 [ 90418-93-2 ]

* 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 [ 90418-93-2 ]
Downstream synthetic route of [ 90418-93-2 ]

[ 90418-93-2 ] Synthesis Path-Upstream 1~11

1
[ 557-21-1 ]
[ 1006-99-1 ]
[ 90418-93-2 ]

Yield	Reaction Conditions	Operation in experiment
81%	With dmap; 1,1'-bis-(diphenylphosphino)ferrocene; nickel(II) chloride hexahydrate; zinc In acetonitrile at 80℃; for 3.5 h; Inert atmosphere; Sealed tube	General procedure: Under argon protection, NiCl2·6H2O (0.05mmo 1,11.9mg), dppf (0.06mmol, 33.3mg), Ζn (0·2mmol, 13.0mg), DMAP (1.0mmol, 122.2mg), Ζn(CN)2 (0.8mmol) , 93.9mg),p-Chloroanisole (1.0 mmol, 140.6 mg) and acetonitrile (5.0 mL) were sequentially added in a 25.0 mL sealed tube, then directly put it into the oil bath at 60 °C, and heating was stopped after 6h, and cooled to room temperature, the reaction solution was directly filtered through a short silica gel column, washed with dichloromethane, concentrated and purified by silica gel column chromatography( given that the product is most easily pulled out, in order to avoid loss of sample mix, unless otherwise noted, both are wet method). Eluent: petroleum ether / ethyl acetate = 20:1, the product was 117.2 mg as a white solid, yield 88percent, and 1H NMR purity was greater than 98percent.

Reference： [1] Organic Letters, 2017, vol. 19, # 8, p. 2118 - 2121
[2] Patent: CN108623495, 2018, A, . Location in patent: Paragraph 0043; 0045; 0222-0224

2
[ 63837-11-6 ]
[ 557-21-1 ]
[ 90418-93-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	at 80℃; for 16 h;	Commercially available 5-bromo-2-methylbenzothiazole (1.42 g), zinc(II) cyanide (584 mg) and tetrakis(triphenylphosphine)palladium(0) (360 mg) were dissolved in dry DMF (12 mL), degassed and stirred at 80° C. under argon. After 16 h the mixture was evaporated and diluted with chloroform. The solution was washed with 1N hydrochloric acid, 1N sodium hydroxide and brine, dried (MgSO₄) and absorbed on silica. Purification by column chromatography (cyclohexane/EtOAc, 8:2 to 7:3) afforded the intermediate (1.01 g; 93percent) as bright yellow needles.

Reference： [1] Patent: US2006/173183, 2006, A1, . Location in patent: Page/Page column 97

3
[ 1006-99-1 ]
[ 90418-93-2 ]

Reference： [1] Organic Letters, 2011, vol. 13, # 4, p. 648 - 651

4
[ 90414-61-2 ]
[ 557-21-1 ]
[ 90418-93-2 ]

Reference： [1] Patent: WO2006/68592, 2006, A1, . Location in patent: Page/Page column 19

5
[ 63837-11-6 ]
[ 90418-93-2 ]

Reference： [1] Patent: US5576343, 1996, A,

6
[ 1006-99-1 ]
[ 75-86-5 ]
[ 90418-93-2 ]

Reference： [1] Organic Process Research and Development, 2016, vol. 20, # 8, p. 1540 - 1545

7
[ 23997-94-6 ]
[ 90418-93-2 ]

Reference： [1] Angewandte Chemie - International Edition, 2010, vol. 49, # 47, p. 8918 - 8922

8
[ 13382-43-9 ]
[ 90418-93-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6205 - 6211

9
[ 90414-61-2 ]
[ 557-21-1 ]
[ 90418-93-2 ]

Reference： [1] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6205 - 6211

10
[ 143-33-9 ]
[ 90418-93-2 ]

Reference： [1] Zhurnal Obshchei Khimii, 1952, vol. 22, p. 2209,2214; engl. Ausg. S. 2267, 2271

11
[ 90418-93-2 ]
[ 24851-69-2 ]

Reference： [1] Zhurnal Obshchei Khimii, 1952, vol. 22, p. 2209,2214; engl. Ausg. S. 2267, 2271
[2] Patent: WO2006/68592, 2006, A1, . Location in patent: Page/Page column 19
[3] Bioorganic and Medicinal Chemistry Letters, 2012, vol. 22, # 19, p. 6205 - 6211

[ 90418-93-2 ] Synthesis Path-Downstream 1~25

1
[ 90418-93-2 ]
[ 24851-69-2 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; water; for 12h;Heating / reflux;	A solution of 2-methyl-5-aminobenzothiazole (10.0 g, 61.1 mmol) in acetone (250 mL) was cooled to 0 C, and concentrated HCl (13.5 mL) was added. A solution OfNaNO2 (5.22 g, 75.7 mmol) in water (75.0 mL) was added in one portion to the first solution. The resulting mixture was stirred for 3 minutes, and a solution of KI (20.4 g, 123 mmol) in water (75.0 mL) was added. The mixture was stirred for an additional 10 minutes and then concentrated under reduced pressure to yield a residue, which was dissolved in a 9: 1 mixture of DCM and MeOH and washed with a saturated solution OfNaHCO3. The organic fraction was washed with brine, dried with Na2SO4, filtered, concentrated under reduced pressure and dried under high vacuum. The resulting iodide, ZnCN2 (7.17 g, 61.1 mmol) and Pd(PPh3)4 (2.00 g, 1.73 mmol) were mixed in DMF (200 mL) and heated to 100 C for 12 hours, under a N2 atmosphere. The solution was then cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM and washed with a saturated solution OfNaHCO3 followed by brine. The organic phase was dried with Na2SO4, filtered and concentrated under reduced pressure to yield the nitrile. 1R NMR (400 MHz, CHLOROFORM-D) delta ppm 2.89 (s, 3 H) 7.58 (dd, J=8.40, 1.56 Hz, 1 H) 7.93 (d, J=8.20 Hz, 1 H) 8.22 (d, J=0.98 Hz3 1 H); MS [M+] calcd. 174.0, found 174.8. A solution of the nitrile in 6.70 N HCl (150 mL) was refluxed for 12 hours. The solution was cooled to room temperature and then concentrated under reduced pressure. The product was purified by flash chromatography on reverse phase silica gel eluting with mixtures of EtOH and water (15/85 to 90/10) (4.45 g, 19.5 mmol, 32% for 3 steps). 1H NMR (600 MHz, DMSO-D6) delta ppm 2.81 (s, 3 H) 7.92 (d, J=8.45 Hz, 1 H) 8.14 (d, J=8.45 Hz, 1 H) 8.38 (s, 1 H); MS [M+] cacld. 193.0, found 193.8.

Reference： [1]Zhurnal Obshchei Khimii,1952,vol. 22,p. 2209,2214; engl. Ausg. S. 2267, 2271
[2]Patent: WO2006/68592,2006,A1 .Location in patent: Page/Page column 19
[3]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 6205 - 6211

2
[ 143-33-9 ]
diazotiertes 2-Methyl-benzothiazol-5-ylamin [ No CAS ]
[ 90418-93-2 ]

Reference： [1]Zhurnal Obshchei Khimii,1952,vol. 22,p. 2209,2214; engl. Ausg. S. 2267, 2271

3
[ 90418-93-2 ]
[ 150610-37-0 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2099 - 2114

4
[ 90418-93-2 ]
[ 150611-03-3 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2099 - 2114

5
[ 90418-93-2 ]
3-(5-amidino-1,3-benzothiazol-2-yl)-2-{4-[(3S)-pyrrolidin-3-yloxy]phenyl}propanoic acid dihydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2099 - 2114

6
[ 90418-93-2 ]
3-(5-amidino-1-benzothiazol-2-yl)-2-{4-[(3S)-1-ethanimidoylpyrrolidin-3-yloxy]phenyl}propanoic acid dihydrochloride [ No CAS ]

Reference： [1]Bioorganic and Medicinal Chemistry,2004,vol. 12,p. 2099 - 2114

7
[ 90418-93-2 ]
[ 24424-99-5 ]
[ 943845-63-4 ]

Yield	Reaction Conditions	Operation in experiment
		The intermediate from Step A above (1.01 g), di-tert-butyl dicarbonate (2.54 g) and nickel(II) chloride hexahydrate (140 mg) were dissolved in dry methanol (60 mL) and cooled to 0 C. Then sodium borohydride (1.6 g) was added in portions and the ice bath was removed. The mixture was vigorously stirred for 5 h, then diethylenetriamine (500 muL) was added and the mixture was concentrated to dryness. The residue was diluted with ethyl acetate, washed with 10% citric acid, saturated sodium hydrogen carbonate and brine, dried (MgSO4) and concentrated. Purification by column chromatography (silica, cyclohexane/EtOAc, 8:2 to 6:4) afforded a yellow oil, which was suspended in hydrogen chloride (4M solution in dioxane, 20 mL) and stirred overnight, filtered and washed with diethyl ether to afford the title compound (455 mg; 37%) as a colourless solid. [M-NH3Cl]+=162; [M-Cl]+=179.

Reference： [1]Patent: US2006/173183,2006,A1 .Location in patent: Page/Page column 97

8
[ 63837-11-6 ]
[ 557-21-1 ]
[ 90418-93-2 ]

Yield	Reaction Conditions	Operation in experiment
93%	tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 80℃; for 16h;	Commercially available <strong>[63837-11-6]5-bromo-2-methylbenzothiazole</strong> (1.42 g), zinc(II) cyanide (584 mg) and tetrakis(triphenylphosphine)palladium(0) (360 mg) were dissolved in dry DMF (12 mL), degassed and stirred at 80 C. under argon. After 16 h the mixture was evaporated and diluted with chloroform. The solution was washed with 1N hydrochloric acid, 1N sodium hydroxide and brine, dried (MgSO4) and absorbed on silica. Purification by column chromatography (cyclohexane/EtOAc, 8:2 to 7:3) afforded the intermediate (1.01 g; 93%) as bright yellow needles.

Reference： [1]Patent: US2006/173183,2006,A1 .Location in patent: Page/Page column 97

9
[ 90414-61-2 ]
[ 557-21-1 ]
[ 90418-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	tetrakis(triphenylphosphine) palladium(0); In N,N-dimethyl-formamide; at 100.0℃; for 12.0h;	A solution of 2-methyl-5-aminobenzothiazole (10.0 g, 61.1 mmol) in acetone (250 mL) was cooled to 0 C, and concentrated HCl (13.5 mL) was added. A solution OfNaNO2 (5.22 g, 75.7 mmol) in water (75.0 mL) was added in one portion to the first solution. The resulting mixture was stirred for 3 minutes, and a solution of KI (20.4 g, 123 mmol) in water (75.0 mL) was added. The mixture was stirred for an additional 10 minutes and then concentrated under reduced pressure to yield a residue, which was dissolved in a 9: 1 mixture of DCM and MeOH and washed with a saturated solution OfNaHCO3. The organic fraction was washed with brine, dried with Na2SO4, filtered, concentrated under reduced pressure and dried under high vacuum. The resulting iodide, ZnCN2 (7.17 g, 61.1 mmol) and Pd(PPh3)4 (2.00 g, 1.73 mmol) were mixed in DMF (200 mL) and heated to 100 C for 12 hours, under a N2 atmosphere. The solution was then cooled to room temperature, and the solvent was evaporated under reduced pressure. The residue was dissolved in DCM and washed with a saturated solution OfNaHCO3 followed by brine. The organic phase was dried with Na2SO4, filtered and concentrated under reduced pressure to yield the nitrile. 1R NMR (400 MHz, CHLOROFORM-D) delta ppm 2.89 (s, 3 H) 7.58 (dd, J=8.40, 1.56 Hz, 1 H) 7.93 (d, J=8.20 Hz, 1 H) 8.22 (d, J=0.98 Hz3 1 H); MS [M+] calcd. 174.0, found 174.8. A solution of the nitrile in 6.70 N HCl (150 mL) was refluxed for 12 hours. The solution was cooled to room temperature and then concentrated under reduced pressure. The product was purified by flash chromatography on reverse phase silica gel eluting with mixtures of EtOH and water (15/85 to 90/10) (4.45 g, 19.5 mmol, 32% for 3 steps). 1H NMR (600 MHz, DMSO-D6) delta ppm 2.81 (s, 3 H) 7.92 (d, J=8.45 Hz, 1 H) 8.14 (d, J=8.45 Hz, 1 H) 8.38 (s, 1 H); MS [M+] cacld. 193.0, found 193.8.

Reference： [1]Patent: WO2006/68592,2006,A1 .Location in patent: Page/Page column 19

10
[ 90418-93-2 ]
[ 34241-39-9 ]
[ 150610-37-0 ]

Yield	Reaction Conditions	Operation in experiment
	With N-Bromosuccinimide; In tetrachloromethane; toluene;	b) 7.46 g of <strong>[90418-93-2]2-methyl-5-benzothiazolecarbonitrile</strong> obtained in the above step a) was dissolved in 250 ml of carbon tetrachloride, and the solution was subjected to reflux under a light irradiation condition. To the resulting reaction solution was gradually added a mixture consisting of 7.62 g of N-bromosuccinimide and 150 mg of 2,2-azobis-iso-butylonitrile, followed by refluxing under heating for 20 hours. After cooling, insoluble materials were removed by filtration, and the solvent was distilled off. Thereafter, the residue thus formed was purified by silica gel column chromatography using toluene as an elution solvent, thereby obtaining 2.18 g of the title compound in the form of light yellow prism crystals. mp: 185-186 C. 1 H-NMR (CDCl3) delta: 4.83 (2H, s), 7.67 (1H, dd), 8.02 (1H, d), 8.34 (1H, d)

Reference： [1]Patent: US5576343,1996,A

11
[ 63837-11-6 ]
copper(l) cyanide [ No CAS ]
[ 90418-93-2 ]

Yield	Reaction Conditions	Operation in experiment
	With ethylenediamine; In 1-methyl-pyrrolidin-2-one; nitrogen; water;	a) 28.0 g of <strong>[63837-11-6]5-bromo-2-methylbenzothiazole</strong> was dissolved in 200 ml of N-methyl-2-pyrrolidone, the solution thus prepared was mixed with 13.8 g of cuprous cyanide and a catalytically effective amount of copper sulfate, and the mixture was stirred for 4 hours with heating at a temperature of 180 to 190 C. in a stream of nitrogen. The resulting reaction solution was poured into water, and insoluble materials thus formed were collected by filtration. The thus collected insoluble materials were mixed with a mixture consisting of 22 ml of ethylenediamine and 50 ml of water, and the resulting mixture was stirred thoroughly. After extraction with benzene, the resulting organic layer was washed with water, and dried to distill of benzene. Thereafter, the residue thus formed was washed with ethanol to obtain 10.22 g of 2-methyl-5-benzothiazolecarbonitrile in the form of light brown crystals. mp: 158-160 C. 1 H-NMR (CDCl3) delta: 2.90 (3H, s), 7.60 (1H, dd), 7.95 (1H, d), 8.25 (1H, d)

Reference： [1]Patent: US5576343,1996,A

12
[ 23997-94-6 ]
[ 90418-93-2 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 8918 - 8922

13
potassiumhexacyanoferrate(II) trihydrate [ No CAS ]
C₉H₉NO₄S [ No CAS ]
[ 90418-93-2 ]

Reference： [1]Angewandte Chemie - International Edition,2010,vol. 49,p. 8918 - 8922

14
[ 1006-99-1 ]
potassiumhexacyanoferrate(II) trihydrate [ No CAS ]
[ 90418-93-2 ]

Reference： [1]Organic Letters,2011,vol. 13,p. 648 - 651

15
[ 13382-43-9 ]
[ 90418-93-2 ]