7724-12-1|6-Amino-2-cyanobenzothiazole| Ambeed

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Quality Control of [ 7724-12-1 ] Purity: 95% SDS Specification

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Product Details of [ 7724-12-1 ]

CAS No. :	7724-12-1
Formula :	C₈H₅N₃S
M.W :	175.21
SMILES Code :	NC1=CC=C2N=C(SC2=C1)C#N
MDL No. :	MFCD11040279
InChI Key :	ZOHSEULTWOYIMS-UHFFFAOYSA-N
Pubchem ID :	14157112

Safety of [ 7724-12-1 ]

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

Computational Chemistry of [ 7724-12-1 ] 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	2.0
Num. H-bond donors	1.0
Molar Refractivity	48.74
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	90.94 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.46
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	1.67
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.76
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	2.36
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.49

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.53
Solubility	0.513 mg/ml ; 0.00293 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.	-3.19
Solubility	0.112 mg/ml ; 0.00064 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	-2.69
Solubility	0.354 mg/ml ; 0.00202 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.	-6.18 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)	2.37

Application In Synthesis of [ 7724-12-1 ]

* 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 [ 7724-12-1 ]

[ 7724-12-1 ] Synthesis Path-Downstream 1~35

1
[ 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.

2
[ 7724-12-1 ]
[ 921-01-7 ]
[ 118969-27-0 ]

References: [1]Journal of the American Chemical Society,1966,vol. 88,p. 2015 - 2019.
[2]Chemical Science,2016,vol. 8,p. 214 - 222.

4
[ 7724-12-1 ]
[ 934270-86-7 ]

Yield	Reaction Conditions	Operation in experiment
29%		(D) Synthesis of 2-cyano-6-methylaminobenzothiazole (5) Formaldehyde (37percent (v/v), 48 mg, 0.60 mmol) dissolved in tetrahydrofuran (THF, 20 mL) was added with 180 mmol/L sulfuric acid (3.2 mL, 0.6 mmol), and stirred at room temperature for several minutes. Compound 4 (99 mg, 0.57 mmol) and sodium borohydride (23 mg, 0.62 mmol) were dissolved in THF (40 mL), and added to the reaction mixture, and the mixture was stirred at room temperature. After progression of the reaction was confirmed by thin layer chromatography (developing solvent: ethyl acetate/n-hexane=2/1), the reaction mixture was added with purified water, and then added with saturated brine, and the aqueous layer was separated from the THF layer. The aqueous layer was extracted 5 times with ethyl acetate, the organic layer was mixed with the THF layer, and this organic solvent layer was dried over anhydrous sodium sulfate, then concentrated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: ethyl acetate/n-hexane=1/8 to 1/6) to obtain Compound 5 (66 mg, 29percent yield). 1H-NMR (300 MHz, CDCl3) delta 2.94 (d, 3H, J=5.1 Hz), 4.27 (br, 1H), 6.88 (dd, 1H, J=2.4, 8.9 Hz), 6.92 (d, 1H, J=2.4 Hz), 7.92 (d, 1H, J=8.9 Hz). 13C-NMR (75 MHz, CDCl3) delta 30.4, 99.2, 113.9, 116.8, 125.4, 129.5, 138.8, 144.6, 149.9. MS (EI+) 189, M+.

References: [1]Patent: US2007/155806,2007,A1 .Location in patent: Page/Page column 5-6.

5
[ 7724-12-1 ]
D-(-)-2-(6'-methylamino-2'-benzothiazolyl)-Δ2-thiazoline-4-carboxylic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		E) Synthesis of N-methylaminoluciferin (10); D-Cysteine hydrochloride monohydrate (102 mg, 0.58 mmol) was dissolved in purified water degassed with argon, and its pH was adjusted to 7.9 with a 0.5 mol/L potassium carbonate solution to prepare D-cysteine solution. Compound 4 (45 mg, 0.24 mmol) was dissolved in methanol (15 mL) degassed with argon, and added with the D-cysteine solution. After argon substitution, the mixture was stirred at room temperature under light shielding condition. The reaction mixture's pH was adjusted to about 4 by adding several drops of hydrochloric acid, and methanol was evaporated. The remaining aqueous layer was extracted 3 times with ethyl acetate. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by preparative HPLC (Eluent A=water/0.1percent trifluoroacetic acid, Eluent B=80percent acetonitrile/20percent water/0.1percent trifluoroacetic acid, A/B=80/20 to 20/80 (20 minutes)) (54 mg, 78percent yield) and recrystallized from ethanol/n-hexane to obtain Compound 10. M.p. 132-134° C. (dec.). 1H-NMR (300 MHz, CD3OD) delta 2.84 (s, 3H), 3.67-3.78 (m, 2H), 5.35 (t, 1H, J=9.1 Hz), 6.88 (dd, 1H, J=2.3, 9.0 Hz), 6.99 (d, 1H, J=2.3 Hz), 7.75 (d, 1H, J=9.0 Hz). 13C-NMR (75 MHz, CD3OD) delta 32.0, 35.8, 79.2, 104.3, 118.0, 125.7, 140.0, 147.9, 148.5, 157.0, 167.9, 173.3. HRMS (ESI+) Calcd for [M+H]+: 294.0371, Found: 294.0340. Anal. Calcd for C12H11N3O2S2*0.25H2O: C, 48.4; H, 3.9; N, 14.1, Found: C, 48.5; H, 4.2; N, 13.7.

References: [1]Patent: US2007/155806,2007,A1 .Location in patent: Page/Page column 6.
[2]Chemistry - An Asian Journal,2011,vol. 6,p. 1800 - 1810.

6
[ 7724-12-1 ]
2-cyano-N,N-dimethylaminobenzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
54%		(F) Synthesis of 2-cyano-N-dimethylaminobenzothiazole (6) Formaldehyde (37percent (v/v), 390 mg, 4.85 mmol) was dissolved in tetrahydrofuran (THF, 20 mL), and added with 180 mmol/L sulfuric acid (3.7 mL, 0.7 mmol), and the mixture was stirred at room temperature for several minutes. Compound 4 (119 mg, 0.68 mmol) and sodium borohydride (26 mg, 0.70 mmol) were dissolved in THF (40 mL), and added to the reaction mixture, and the mixture was stirred at room temperature. After progression of the reaction was confirmed by thin layer chromatography (developing solvent: ethyl acetate/n-hexane=2/1), the reaction mixture was added with purified water, then added with saturated brine, and the aqueous layer was separated from the THF layer. After the aqueous layer was extracted 5 times with ethyl acetate, the organic layer was mixed with the THF layer, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography (developing solvent: ethyl acetate/n-hexane =1/6 to 1/4) to obtain Compound 6 (74 mg, 54percent yield). 1H-NMR (300 MHz, CDCl3) delta 3.10 (s, 6H), 7.01 (d, 1H, J=2.6 Hz), 7.06 (dd, 1H, J=2.6, 9.2 Hz), 7.98 (d, 1H, J=9.2 Hz). 13C-NMR (75 MHz, CDCl3) delta 40.6, 100.7, 114.0, 114.8, 125.1, 129.4, 138.6, 143.8, 150.6. MS (EI+) 203, M+.

References: [1]Patent: US2007/155806,2007,A1 .Location in patent: Page/Page column 6.

7
[ 7724-12-1 ]
[ 934270-96-9 ]

Yield	Reaction Conditions	Operation in experiment
29%		(C) Synthesis of 2-cyano-6-(4'-benzyloxycarbonylamidophenethyl)-aminobenzothiazole (18) Compound 17 (376 mg, 1.40 mmol) was dissolved in THF (70 mL), and the solution was added with 180 mmol/L sulfuric acid (8 mL, 1.4 mmol), and stirred at room temperature for several minutes. The mixture was added with Compound 4 and sodium borohydride (54 mg, 1.43 mmol) dissolved in THF (60 mL) were added to mixture, and stirred at room temperature. After progression of the reaction was confirmed by thin layer chromatography (developing solvent: ethyl acetate/n-hexane=2/1), the reaction mixture was added with purified water and added with saturated brine, then the aqueous layer was separated from the THF layer. After the aqueous layer was extracted 5 times with ethyl acetate, the organic layer was mixed with the THF layer, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified twice by silica gel chromatography (developing solvent: ethyl acetate/n-hexane=1/6 to 1/4 to 1/2) to obtain Compound 18 (157 mg, 29percent yield). 1H-NMR (300 MHz, CDCl3) delta 2.93 (t, 2H, J=6.9 Hz), 3.45 (td, 2H, J=6.1, 6.9 Hz), 4.19 (br, 1H), 5.20 (s, 2H), 6.66 (br, 1H), 6.83 (dd, 1H, J=2.3, 9.0 Hz), 6.93 (d, 1H, J=2.3 Hz), 7.16 (td, 2H, J=1.8, 8.4 Hz), 7.29-7.43 (m, 7H), 7.90 (d, 1H, J=9.0 Hz). 13C-NMR (75 MHz, CDCl3) delta 34.2, 44.6, 66.8, 99.8, 113.8, 116.9, 119.1, 125.3, 127.9, 128.1, 128.2, 128.4, 129.1, 133.5, 135.9, 136.4, 138.6, 144.5, 148.7, 153.4. HRMS (ESI+) Calcd for [M+Na]+: 451.1205, Found: 451.1243.

References: [1]Patent: US2007/155806,2007,A1 .Location in patent: Page/Page column 8.

8
[ 7724-12-1 ]
tert-butyl 6-(2-cyanobenzo[d]thiazol-6-ylamino)-6-oxohexylcarbamate [ No CAS ]
[ 6404-29-1 ]
[ 543-27-1 ]
4-(6-(2-cyanobenzo[d]thiazol-6-ylamino)-6-oxohexylcarbamoyl)-2-(3-(dimethylamino)-6-(dimethyliminio)-6H-xanthen-9-yl)benzoate [ No CAS ]