22514-58-5|2-Bromobenzo[d]thiazole-6-carboxylic acid| Ambeed

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Quality Control of [ 22514-58-5 ] Purity: 95% SDS Specification

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Product Details of [ 22514-58-5 ]

CAS No. :	22514-58-5
Formula :	C₈H₄BrNO₂S
M.W :	258.09
SMILES Code :	BrC1=NC2=C(S1)C=C(C=C2)C(=O)O
MDL No. :	MFCD09266217
InChI Key :	ICKXPLAJDFRFME-UHFFFAOYSA-N
Pubchem ID :	45789628

Safety of [ 22514-58-5 ]

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

Computational Chemistry of [ 22514-58-5 ] Show Less

Physicochemical Properties

Num. heavy atoms	13
Num. arom. heavy atoms	9
Fraction Csp3	0.0
Num. rotatable bonds	1
Num. H-bond acceptors	3.0
Num. H-bond donors	1.0
Molar Refractivity	54.28
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	78.43 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	1.71
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	2.85
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.76
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.	1.77
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	3.16
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.45

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.68
Solubility	0.0537 mg/ml ; 0.000208 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.	-4.16
Solubility	0.018 mg/ml ; 0.0000699 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately 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	-3.2
Solubility	0.163 mg/ml ; 0.000632 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	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.	-5.85 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	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.56

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<0.0
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)	2.17

Application In Synthesis of [ 22514-58-5 ]

* 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 [ 22514-58-5 ]

[ 22514-58-5 ] Synthesis Path-Downstream 1~26

2
[ 22514-58-5 ]
[ 75-65-0 ]
[ 945400-88-4 ]

Yield	Reaction Conditions	Operation in experiment
	With diphenylphosphoranyl azide; triethylamine; at 80℃; for 4.0h;	Triethylamine (1.94 mL, 13.9 mmol) and diphenylphosphoryl azide (2.76 niL, 12.8 mmol) were added to a solution of 2-bromo-l,3-benzothiazole-6-carboxylic acid (3.0 g, 11.6 mmol) in tert-butanol (100 mL) and the reaction mixture was stirred at 80 0C for 4 h. The solvent was evaporated under reduced pressure and the residue was subjected to flash chromatography (Heptane/EtOAc gradient) to give tert-butyl (2-bromo-l,3-benzothiazol- 6-yl)carbamate (1.1 g) as a white solid. MS m/z (M+H) 329, 331.

References: [1]Patent: WO2007/86800,2007,A1 .Location in patent: Page/Page column 100.

3
[ 22514-58-5 ]
C₈H₃BrClNOS [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With thionyl chloride; at 20 - 60℃; for 1.5h;	2-Bromo-l,3-benzothiazole-6-carboxylic acid (100 mg, 0.39 mmol) and thionyl chloride (2 mL) were mixted and stirred at rt for 1 h then at 60 0C for 30 min. The mixture was <n="100"/>concentrated under reduced pressure and the residue was dissolved in CHCl3 (3 niL). This solution was added dropwise to NH3 (ca. 7 N in MeOH, 5 mL) at 0 0C. The mixture was stirred at rt for 1 h before it was concentrated under reduced pressure. The crude product was partitioned between EtOAc and H2O. The aqueous layer was extracted with EtOAc and the organic phase was dried (Na2SO4) and concentrated to give the the product (77 mg) as a white solid. MS m/z (M+H) 213, (M-H) 211.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; for 3.0h;Cooling with ice;	STEP A: <strong>[22514-58-5]2-Bromo-6-benzothiazolecarboxylic acid</strong> (496.0 mg, 192 mmol) was suspended in dichloromethane (15 mL), cooled in ice bath, then treated with 2M oxalyl chloride in dichloromethane (2 mL, 4 mmol) and 1 drop of dimethylformamide. The resulting homogenous mixture was stirred for 3 h, then concentrated to a solid. The solid was dissolved in dichloromethane (20 mL), the resulting solution was cooled in an ice bath, then treated with diisopropylethylamine (0.45 mL, 2.58 mmol) and 4-aminoveratole (323.9 mg, 2.11 mmol). The resulting mixture was stirred overnight at room temperature, then diluted with dichloromethane, washed with water, washed with brine, dried over sodium sulfate, filtered and concentrated to yield 2-bromo-N-(3,4-dimethoxyphenyl)benzo[d]thiazole-6-carboxamide as a brown solid. 1HNMR (DMSO-d6) delta 10.3 (s, 1H), 8.69 (s, 1H), 8.10 (s, 2H), 7.47 (d, J=2.23 Hz, 1H), 7.37-7.33 (m, 1H), 6.94 (d, J=8.73 Hz, 1H), 3.76 (s, 3H), 3.75 (s, 3H). MS MH+=393.
	With oxalyl dichloride;N,N-dimethyl-formamide; In dichloromethane; at 20℃; for 1.0h;	2-Chloro-benzothiazole-6-carboxylic acid r2-methyl-5-(3-trifluoromethyl-benzoylamino)- phenyll -amide[0100] To a solution of <strong>[22514-58-5]2-bromo-benzothiazole-6-carboxylic acid</strong> (984 mg, 3.81 mmol) in CH2Cl2 (40 mL) is added DMF (70 muL) and oxalyl chloride (6.6 mL, 76 mmol). After the addition is complete, the reaction is stirred at rt for an additional hour. After solvent removal in vacuo, the crude product is used without further purification. The corresponding acetyl chloride <n="36"/>is dissolved in 20 mL CH2Cl2. The solution is added via cannula to a solution of N-(3-amino-4- methyl-phenyl)-3-trifluoromethyl-benzamide (1.12 g, 3.81 mmol) and diisopropanylethylamine (1.65 mL, 9.52 mmol) in 40 mL CH2Cl2 at 0 0C over 30 min. The mixture is stirred at rt for 1 h. The mixture is extracted with ethyl acetate. The organic phase is washed with saturated nuaHCU3 solution and brine. The solvent is removed in vacuo and the crude product is purified by recrystallization (hexane:CH2Cl2/10:l) to give 2-chloro-benzothiazole-6-carboxylic acid [2- methyl-5-(3-trifluoromethyl-benzoylamino)-phenyl]-amide. 1H NMR (400 MHz, DMSO) delta 10.50 (s, IH), 10.12 (s, IH), 8.75 (s, IH), 8.30 (s, IH), 8.26 (d, IH), 8.13 (s, 2H), 7.97 (d, IH), 7.87 (d, IH), 7.78 (d, IH), 7.61 (dd, IH), 7.29 (d, IH), 2.24 (s, 3H). MS(ESI) m/z: 490.1 (M+ 1)

References: [1]Patent: WO2007/86800,2007,A1 .Location in patent: Page/Page column 98-99.
[2]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2324 - 2328.
[3]Patent: US2011/152287,2011,A1 .Location in patent: Page/Page column 18.
[4]Patent: WO2008/124393,2008,A1 .Location in patent: Page/Page column 33; 34-35.

4
[ 1024583-33-2 ]
[ 22514-58-5 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2008,vol. 18,p. 2324 - 2328.

5
[ 66947-92-0 ]
[ 22514-58-5 ]

Yield	Reaction Conditions	Operation in experiment
99%		2-Bromo-benzothiazole-6-carboxylic acid; [00105] To a solution of 2-bromo-benzothiazole-6-carboxylic acid methyl ester (1.256 g, 4.39 mmol) in THF (60 mL) and H2O (20 mL) is added lithium hydroxide monohydrate (920 mg, 21.9 mmol) at 0 0C. The mixture is stirred at rt overnight. The mixture is treated with IN HCl solution to adjust pH to 2 and extracted with ethyl acetate. The organic phase is washed with brine. The solvent is removed in vacuo and the crude product is used for next step without further purification. MS(ESI) m/z: 257.9 (M+l) +.

References: [1]Patent: WO2008/124393,2008,A1 .Location in patent: Page/Page column 33-34.

6
[ 22514-58-5 ]
[ 18107-18-1 ]
[ 1024583-33-2 ]

Yield	Reaction Conditions	Operation in experiment
	In methanol; dichloromethane; at 20℃;Cooling with ice;	STEP A: <strong>[22514-58-5]2-Bromo-6-benzothiazolecarboxylic acid</strong> (0.500 g, 1.94 mmol) was suspended in dichloromethane/methanol (12 ml, 6:1) and cooled to 0 C. with an ice-water bath. Then, 2M (trimethylsilyl)diazomethane (2.91 ml, 5.81 mmol) was added dropwise over 5 min. The resulting mixture was warmed to room temperature and stirred at room temperature for 2 hrs. The resulting mixture was concentrated in vacuo to yield methyl 2-bromobenzo[d]thiazole-6-carboxylate. 1HNMR (CDCl3) delta 8.55 (s, 1H), 8.15 (d, J=8.6 Hz, 1H), 8.02 (d, J=8.6 Hz, 1H), 3.07 (s, 3H).

References: [1]Patent: US2011/152287,2011,A1 .Location in patent: Page/Page column 21.

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[ 22514-58-5 ]
[ 1312762-76-7 ]