2406-90-8|2-Chlorobenzo[d]thiazol-6-amine| Ambeed

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Quality Control of [ 2406-90-8 ] Purity: 97% SDS Specification

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Product Details of [ 2406-90-8 ]

CAS No. :	2406-90-8
Formula :	C₇H₅ClN₂S
M.W :	184.65
SMILES Code :	NC1=CC=C2N=C(Cl)SC2=C1
MDL No. :	MFCD08276901
InChI Key :	YPTWPDOGEAHMOR-UHFFFAOYSA-N
Pubchem ID :	10921203

Safety of [ 2406-90-8 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H319-H332-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 2406-90-8 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	0
Num. H-bond acceptors	1.0
Num. H-bond donors	1.0
Molar Refractivity	49.03
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	67.15 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.82
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	2.58
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.54
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.	1.45
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	3.07
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.29

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.22
Solubility	0.112 mg/ml ; 0.000609 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.	-3.64
Solubility	0.0424 mg/ml ; 0.00023 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	-3.23
Solubility	0.109 mg/ml ; 0.000593 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	Yes
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	Yes
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.	-5.59 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	1.0 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)	2.36

Application In Synthesis of [ 2406-90-8 ]

* 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 [ 2406-90-8 ]

[ 2406-90-8 ] Synthesis Path-Downstream 1~36

1
[ 108-30-5 ]
[ 2406-90-8 ]
[ 99852-26-3 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1953,vol. 73,p. 219,221.
Chem.Abstr.,1954,p. 2043.

2
[ 2406-90-8 ]
[ 996-82-7 ]
(6-amino-benzothiazol-2-yl)-malonic acid diethyl ester [ No CAS ]

References: [1]Pharmaceutical Bulletin,1953,vol. 1,p. 319,321.

3
[ 2406-90-8 ]
[ 108-24-7 ]
[ 7714-22-9 ]

References: [1]Journal of Organic Chemistry,2018,vol. 83,p. 7467 - 7479.
[2]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1947,vol. 67,p. 37.
Chem.Abstr.,1951,p. 9529.
[3]Journal of the American Chemical Society,1966,vol. 88,p. 2015 - 2019.

4
[ 2406-90-8 ]
[ 99-61-6 ]
[ 58599-93-2 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1952,vol. 72,p. 1492.
Chem.Abstr.,1953,p. 8062.

5
[ 2406-90-8 ]
[ 122-85-0 ]
acetic acid-{4-[(2-chloro-benzothiazol-6-ylimino)-methyl]-anilide} [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1951,vol. 71,p. 902,904.
Chem.Abstr.,1952,p. 8091.

6
[ 2406-90-8 ]
[ 75-36-5 ]
[ 7714-22-9 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 4007,4009.

7
[ 2406-90-8 ]
[ 98-09-9 ]
N-(2-chloro-benzothiazol-6-yl)-benzenesulfonamide [ No CAS ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 4007,4009.

8
[ 2406-90-8 ]
[ 121-60-8 ]
N-acetyl-sulfanilic acid-(2-chloro-benzothiazol-6-ylamide) [ No CAS ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1947,vol. 67,p. 37.
Chem.Abstr.,1951,p. 9529.

9
[ 2406-90-8 ]
[ 77563-27-0 ]

References: [1]Yakugaku Zasshi/Journal of the Pharmaceutical Society of Japan,1947,vol. 67,p. 123.
Chem.Abstr.,1951,p. 9530.

10
[ 2406-90-8 ]
[ 53306-17-5 ]

References: [1]Journal of the American Chemical Society,1951,vol. 73,p. 4007,4009.

11
[ 2407-11-6 ]
[ 2406-90-8 ]

Yield	Reaction Conditions	Operation in experiment
83%		To a solution of 2-CHLOROBENZOTHIAZOLE (12.0 g, 70.7 MMOL) in concentrated H2SO4 (60 mL) was added HN03 (69% solution, 6 mL) dropwise at 0C for 20 min. The mixture was stirred at 5C for 3h, poured into ice-water (150 mL). The precipitate was collected and washed with 5% sodium bicarbonate and water, dried in VACUO.'H NMR analysis showed the mixture contained 78% 6-nitro-2-chlorobenzothiazole and 8% 5-nitro-2- chlorobenzothiazole. Recrystallization from ethanol gave 6-nitro-2-chlorobenzothiazole as white crystalline solid (11 g, 72%). 3.5 g of the solid was dissolved in refluxing ethanol-acetic acid (150: 15 mL), Iron powder was added in one portion.. The mixture was refluxed for 1.5h, filtered. The filtrate was concentrated in vacuo to half volume and neutralized with 10% NaOH to pH 7.5, extracted with ethyl acetate. The organic phase was washed with brine, dried over magnesium sulphate and evaporated to give a residue, which was RECRYSTALLIZED from ethanol. Light purple crystals (2.5 g, 83%) were obtained. Mp 160-164C ; TLC single spot at Rf 0.27 (30% EtOAc/hexane) ;'HNMR (270 MHz, DMSO-d6) 5 7.58 (1H, d, J = 9.0 Hz, 4-H), 7.03 (1H, d, J = 2.0 Hz, 7-H), 6.77 (1 H, dd, J = 9.0, 2. 0 Hz, 5-H), 5.55 (2H, s, NH2). The mother liquor from the RECRYSTALLIZATION of nitration product was evaporated and subjected to iron powder reduction as described above. The crude product was purified with flash chromatography (ethyl acetate-DCM gradient elution) to give 2-CHLORO- benzothiazol-5-yl-amine as yellow solid. Mp 146-149C ; TLC single spot at Rf 0.52 (10% EtOAc/DCM) ;'HNMR (270 MHZ, DMSO-d6) 8 7.63 (1 H, d, J = 8. 6 HZ, 7-H), 7.05 (1 H, d, J = 2.3 Hz, 4-H), 6.78 (1 H, dd, J = 8.6, 2.3 Hz, 6-H), 5.40 (2H, s, NH2).
61%		(B) Synthesis of 2-chloro-6-aminobenzothiazole (3) Compound 2 (1.96 g, 9.14 mmol) was dissolved in ethanol (150 mL) and purified water (100 mL), and the solution was added with anhydrous tin(II) chloride (20.7 g, 91.7 mmol). The mixture was added with 4.8 mol/L hydrochloric acid (20 mL, 96 mmol) and refluxed at 120 C. After disappearance of the starting materials was confirmed by thin layer chromatography (developing solvent: dichloromethane), the mixture was basified with aqueous sodium hydroxide. The precipitates were removed by filtration, After, ethanol was evaporated, the residue was extracted three times with ethyl acetate. Then organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/1) to obtain Compound 3 as white solid (1.02 g, 61% yield). 1H-NMR (300 MHz, CDCl3) delta 3.85 (br, 2H), 6.81 (dd, 1H, J=2.4, 8.7 Hz), 6.99 (d, 1H, J=2.4 Hz), 7.70 (d, 1H, J=8.7 Hz). MS (ESI+) 185.0, [M+H]+.
33%	With iron; acetic acid; at 40℃; for 5h;	Suspend 2-Chloro-6-nitro-benzothiazole (21.43 g, 99.8 mmol) in glacial acetic acid (30OmL). Add elemental iron (12.9 g, 231 mmol) and stir at 40 0C for 5 h. Filter the reaction mixture through Celite, concentrate in vacuo, and adsorb onto silica gel. Subject the residue to silica gel flash column chromatography in two portions [(120 g column, 0-10% CH3OH/CH2CI2), (120 g column, 0-5% CH3OHZCH2Cl2)] to yield the desired product (6.17 g, 33%). mass spectrum (m/e): 185.0 (M+l).

References: [1]Patent: WO2004/37251,2004,A1 .Location in patent: Page/Page column 99; 100.
[2]Journal of the American Chemical Society,2010,vol. 132,p. 13586 - 13587.
[3]Patent: US2007/155806,2007,A1 .Location in patent: Page/Page column 5.
[4]Chemistry - An Asian Journal,2011,vol. 6,p. 1800 - 1810.
[5]Chemical Communications,2013,vol. 49,p. 8644 - 8646.
[6]Bioorganic and Medicinal Chemistry Letters,2005,vol. 15,p. 3328 - 3332.
[7]Patent: WO2006/66173,2006,A2 .Location in patent: Page/Page column 51.
[8]Zhurnal Obshchei Khimii,1939,vol. 9,p. 409,411.
Chemisches Zentralblatt,1940,vol. 111,p. 545.
[9]Antimicrobial agents and chemotherapy,2002,vol. 46,p. 2588 - 2594.
[10]Mutation Research - Genetic Toxicology and Environmental Mutagenesis,2008,vol. 650,p. 104 - 114.
[11]International Journal of Peptide Research and Therapeutics,2019,vol. 25,p. 1209 - 1215.

12
[ 2406-90-8 ]
[ 463-71-8 ]
[ 56813-37-7 ]

References: [1]Soviet progress in chemistry,1975,vol. 41,p. 87 - 89.
Ukrainskii Khimicheskii Zhurnal (Russian Edition),1975,vol. 41,p. 764 - 767.

13
[ 2406-90-8 ]
[ 151-50-8 ]
[ 7724-12-1 ]

Yield	Reaction Conditions	Operation in experiment
54%	In dimethyl sulfoxide; at 120℃;	(C) Synthesis of 2-cyano-6-aminobenzothiazole (4) Potassium cyanide (1.29 g, 19.7 mmol) was added to dimethyl sulfoxide (DMSO, 150 mL). After argon substitution, the mixture was refluxed overnight at 135° C. with stirring. The temperature was lowered to 120° C., and Compound 3 (1.02 g, 5.55 mmol) dissolved in DMSO (20 mL) was added. After disappearance of the starting materials was confirmed by thin layer chromatography (developing solvent: ethyl acetate/n-hexane=2/1), the reaction mixture was poured into a mixed solution of 1.0 mol/L potassium dihydrogenphosphate solution (100 mL) and diethyl ether, (150 mL), and the diethyl ether layer was separated. The aqueous layer was extracted 5 times with ethyl acetate, the organic layer was mixed with the diethyl ether layer, and this organic solvent layer was washed twice with purified water and twice with saturated brine. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent: ethyl acetate/n-hexane=1/4 to 1/2) to obtain Compound 4 as yellow solid (521 mg, 54percent yield). 1H-NMR (300 MHz, CDCl3) delta 4.13 (br, 2H), 6.96 (dd, 1H, J=2.4, 8.9 Hz), 7.09 (d, 1H J=2.4 Hz), 7.95 (d, 1H, J=8.9 Hz). MS (ESI+) 176.0, [M+H]+.

References: [1]Patent: US2007/155806,2007,A1 .Location in patent: Page/Page column 5.
[2]Journal of the American Chemical Society,1966,vol. 88,p. 2015 - 2019.

14
[ 2406-90-8 ]
[ 407-25-0 ]
[ 7714-24-1 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 2015 - 2019.

15
[ 2406-90-8 ]
[ 87-13-8 ]
[ 33109-79-4 ]

References: [1]Chemical and Pharmaceutical Bulletin,1976,vol. 24,p. 130 - 135.

16
[ 2406-90-8 ]
[ 58263-00-6 ]

References: [1]Soviet progress in chemistry,1975,vol. 41,p. 97 - 98.
Ukrainskii Khimicheskii Zhurnal (Russian Edition),1975,vol. 41,p. 1222 - 1224.

17
[ 75-15-0 ]
[ 106-50-3 ]
[ 2406-90-8 ]

References: [1]Comptes Rendus des Seances de l'Academie des Sciences, Serie C: Sciences Chimiques,1976,vol. 283,p. 319 - 321.

18
[ 2406-90-8 ]
[ 16463-38-0 ]
[ 138962-06-8 ]

References: [1]Tetrahedron Letters,1991,vol. 32,p. 6709 - 6710.

19
[ 58263-00-6 ]
[ 2406-90-8 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1980,p. 2362 - 2370.

20
[ 2406-90-8 ]
[ 88-65-3 ]
[ 138962-06-8 ]

References: [1]Journal of Heterocyclic Chemistry,2002,vol. 39,p. 1083 - 1085.
[2]Synthetic Communications,1995,vol. 25,p. 2443 - 2448.
[3]Mutation Research - Genetic Toxicology and Environmental Mutagenesis,2008,vol. 650,p. 104 - 114.

23
[ 2406-90-8 ]
[ 1655-07-8 ]
2,11-dichloro-7,8,9,10-tetrahydrothiazolo[5,4-a]acridine [ No CAS ]