20358-03-6|2-Amino-5-bromobenzothiazole| Ambeed

Size	Price	VIP Price	US Stock	Global Stock	In Stock
{[ item.pr_size ]}		Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate,item.pr_is_large_size_no_price, item.vip_usd) ]}

US Stock: ship in 0-1 business day
Global Stock: ship in 5-7 days

{[ item.pr_size ]}

In Stock

- +

Please Login or Create an Account to: See VIP prices and availability

US Stock: ship in 0-1 business day
Global Stock: ship in 2 weeks

Quality Control of [ 20358-03-6 ] Purity: 97% SDS Specification

COA

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

NMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

CNMR

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

HPLC

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

LC-MS

Search for reports by entering the product batch number.
Batch number can be found on the product's label following the word 'Batch'.

1-2 Day Shipping
High Quality
Technical Support

Product Details of [ 20358-03-6 ]

CAS No. :	20358-03-6
Formula :	C₇H₅BrN₂S
M.W :	229.10
SMILES Code :	NC1=NC2=C(S1)C=CC(=C2)Br
MDL No. :	MFCD00577806
InChI Key :	ZPUJTWBWSOOMRP-UHFFFAOYSA-N
Pubchem ID :	13775785

Safety of [ 20358-03-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302-H315-H317-H319-H335
Precautionary Statements:	P261-P280-P305+P351+P338

Computational Chemistry of [ 20358-03-6 ] 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	51.72
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.	1.93
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	2.72
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.65
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.	2.01
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	3.1
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.48

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.58
Solubility	0.0603 mg/ml ; 0.000263 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.	-3.78
Solubility	0.0377 mg/ml ; 0.000164 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	-3.47
Solubility	0.0776 mg/ml ; 0.000339 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.	-5.77 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.	0.55

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)	2.13

Application In Synthesis of [ 20358-03-6 ]

* 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 [ 20358-03-6 ]

[ 20358-03-6 ] Synthesis Path-Downstream 1~35

1
[ 20358-03-6 ]
[ 53004-75-4 ]

References: [1]Chemistry of Heterocyclic Compounds,1974,vol. 10,p. 320 - 323.
Khimiya Geterotsiklicheskikh Soedinenii,1974,vol. 10,p. 367 - 371.

2
[ 20358-03-6 ]
6-bromo-benzothiazole-2-diazonium; tetrafluoroborate [ No CAS ]

References: [1]Chemistry of Heterocyclic Compounds,1974,vol. 10,p. 320 - 323.
Khimiya Geterotsiklicheskikh Soedinenii,1974,vol. 10,p. 367 - 371.

3
[ 157645-54-0 ]
[ 20358-03-6 ]

References: [1]Journal of the Chemical Society C: Organic,1969,p. 268 - 272.

4
[ 4394-85-8 ]
[ 20358-03-6 ]
[ 112446-68-1 ]

References: [1]Collection of Czechoslovak Chemical Communications,1987,vol. 52,p. 1006 - 1014.

5
[ 20358-03-6 ]
[ 98-09-9 ]
N-(5-Bromo-benzothiazol-2-yl)-benzenesulfonamide [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 311 - 318.

6
[ 20358-03-6 ]
[ 98-09-9 ]
[ 103-70-8 ]
N-(5-Bromo-benzothiazol-2-yl)-benzenesulfonamide [ No CAS ]
N-[5-Bromo-3-[(E)-phenyliminomethyl]-3H-benzothiazol-(2Z)-ylidene]-benzenesulfonamide [ No CAS ]

References: [1]Collection of Czechoslovak Chemical Communications,1988,vol. 53,p. 311 - 318.

7
[ 20358-03-6 ]
[ 79-04-9 ]
<i>N</i>-(5-bromo-benzothiazol-2-yl)-2-chloro-acetamide [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 1289 - 1294.
[2]Asian Journal of Chemistry,2011,vol. 23,p. 3969 - 3974.

8
[ 20358-03-6 ]
1<i>H</i>-benzoimidazole-2-carboxylic acid (5-bromo-benzothiazol-2-yl)-amide [ No CAS ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1999,vol. 38,p. 1289 - 1294.

9
[ 875-51-4 ]
[ 20358-03-6 ]

References: [1]Journal of the Chemical Society C: Organic,1969,p. 268 - 272.

10
[ 21327-14-0 ]
[ 20358-03-6 ]

Yield	Reaction Conditions	Operation in experiment
	With bromine; In chloroform; at 20℃; for 18.5h;Heating / reflux;	Synthesis of 2-amino-5-bromobenzothiazole (Intermediate 63) A solution of Intermediate 62 (1.29 g) in chloroform (12 ml) was added dropwise with a solution of bromine (272 mul, WAKO) in chloroform (1.5 ml), refluxed with heating for 2.5 hours and then stirred at room temperature for 16 hours.The reaction mixture was concentrated under reduced pressure, neutralized with 5percent aqueous ammonia and then added with water (50 ml) and methylene chloride (150 ml) for extraction.The organic layer was dried, and then the solvent was evaporated under reduced pressure.The residue was purified by column chromatography (Quad, hexane:ethyl acetate=2:1) to obtain the title compound (Intermediate 63, 609 mg).

References: [1]Medicinal Chemistry Research,2012,vol. 21,p. 1136 - 1148.
[2]Patent: US2004/44258,2004,A1 .Location in patent: Page 97.
[3]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331.
[4]Journal of Medicinal Chemistry,2016,vol. 59,p. 9814 - 9824.

11
[ 20358-03-6 ]
[ 5419-55-6 ]
[ 590417-69-9 ]

Yield	Reaction Conditions	Operation in experiment
		Synthesis of methyl 3-[3-(2-aminobenzothiazol-5-yl)-4-cyclopentylmethyloxyphenyl]Propionate (Compound No. 284) (Preparation Method 4, Step d-1) A solution of Intermediate 63 (459.1 mg) in anhydrous THF (30 ml) was added with N,N,N',N'-tetramethylethylenediamine (1.51 ml, WAKO), cooled to -78° C. under argon atmosphere, then added dropwise with 1.62 M solution of t-butyllithium in pentane (7.06 ml) and stirred for 30 minutes.The reaction mixture was added dropwise with (iPrO)3B (2.77 ml), stirred for 30 minutes, then warmed to room temperature and further stirred for 1.5 hours.The reaction mixture was added with 0.5 M aqueous sulfuric acid (7.5 ML) and extracted with diethyl ether (50 ml*3).The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure to obtain crude 2-amino-5-benzothiazoleboronic acid.According to the procedure described in the synthesis method of Compound of Example 001 (Preparation Method 4, Step d-1) with the modifications that the reaction was carried out for 12 hours, and the purification was performed by flash column chromatography (hexane:ethyl acetate=2:1), the above compound was reacted with Intermediate 3 (344 mg), 2 M aqueous sodium carbonate (4.5 ml) and (Ph3P)4Pd (179 mg) and treated to obtain the title compound (Compound No. 284, 76 mg).

References: [1]Patent: US2004/44258,2004,A1 .Location in patent: Page 97-98.

12
[ 20358-03-6 ]
[ 109-90-0 ]
[ 1160789-85-4 ]

Yield	Reaction Conditions	Operation in experiment
50 - 60%	In 1,4-dioxane; at 78 - 80℃; for 16h;Product distribution / selectivity;	To a suspension of 5-bromo-benzothiazol-2-ylamine IV (0.23 g, 1.0 mmol) in 1, 4- dioxane (10 mL) was added ethylisocyanate (0.36 g, 0.38 mL, 5.02 mmol). The reaction mixture was heated up to 78-8O0C overnight. After completion of reaction (TLC monitoring), 1 , 4-dioxane was distilled off and co evaporated with hexane. The resulting solid was treated with water to 60-700C for 3-5 h. The resulting solid was <n="19"/>filtered off and again washed with hot water, dried under high vacuum to obtain the desired product as off-white solid (0.15 g, 50percent). 1H NMR (DMSO-d6, 400 MHz): delta 1.08 (t, J= 7.20 Hz, 3H), 3.18 (m, 2H), 6.70 (br s, 1H), 7.36 (dd, J= 1.60 and 8.0 Hz, 1 H), 7.79 (d, J = 1.60 Hz1 1 H), 7.84 (d, J= 8.40 Hz, 1 H) and 10.85 (br s, 1 H). MS: 300.07 (M+H+).; To a solution of 2-amino-5-bromo benzothiazole (0.23 g, 1.0 mmol) in 1 ,4-dioxane (8.0 mL) was added ethylisocyanate (3.96 ml_, 5.0 mmol) and the resulting solution was heated to 8O0C for 16 h. After the completion of the reaction (TLC monitoring), 1 ,4-dioxane was distilled off followed by co-distillation with n-hexane (2 times). The residue was then stirred with water at 9O0C for 2 h followed by filtration to obtain the desired product that was further washed with hot water and then dried. The residue was finally washed with ether to obtain the desired product (0.18 g, 60percent).

References: [1]Patent: WO2009/74812,2009,A1 .Location in patent: Page/Page column 16; 17-18; 22.

13
[ 854890-84-9 ]
[ 20358-03-6 ]

Yield	Reaction Conditions	Operation in experiment
16%	With sodium hydride; In 1-methyl-pyrrolidin-2-one; at 20 - 160℃; for 1h;	To a solution of 2,5-dibromo-phenyl)-thiourea III (2.0 g, 6.5 mmol) in N- methylpyrrolidone (10 mL) was added NaH (60percent dispersion in mineral oil, 0.24 g, 9.70 mmol) at room temperature. The reaction mixture was heated up to 1600C for 1h. After completion of reaction (TLC monitoring), the reaction mixture was allowed to come to room temperature. Water (100 mL) was added to the reaction mixture and extracted with ethyl acetate (3x 50 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and evaporated to dryness under reduced pressure. The crude residue was purified over silica gel (100 -200M) using hexane and ethyl acetate (80:20) to obtain the desired product as white solid (0.23 g, 16percent). 1H NMR (DMSO-d6, 400 MHz): delta 7.15 (dd, J= 2.0 and 8.40 Hz, 1 H), 7.47 (d, J= 2.0 Hz, 1 H)1 7.62 (d, J= 8.40 Hz, 1 H) and 7.68 (br s, 2H). MS: 229.01 (M+H+).

References: [1]Patent: WO2009/74812,2009,A1 .Location in patent: Page/Page column 16; 17.

14
[ 45891-21-2 ]
[ 20358-03-6 ]
[ 1223564-61-1 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331.

15
[ 20358-03-6 ]
[ 41834-87-1 ]
1-butyryl-3-(5-bromobenzo[d]thiazol-2-yl) thiourea [ No CAS ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331.

16
[ 20358-03-6 ]
[ 68967-37-3 ]
[ 1223564-47-3 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331.

17
[ 20358-03-6 ]
[ 532-55-8 ]
[ 1223564-51-9 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331.

18
[ 20358-03-6 ]
[ 28115-92-6 ]
[ 1223564-43-9 ]

References: [1]European Journal of Medicinal Chemistry,2010,vol. 45,p. 1323 - 1331.

19
C₁₄H₁₀BrN₂OPolS [ No CAS ]
[ 20358-03-6 ]
[ 20358-05-8 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 644 - 648.

20
C₁₄H₈BrN₂OPolS [ No CAS ]
[ 20358-03-6 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2010,vol. 20,p. 644 - 648.

21
[ 20358-03-6 ]
[ 23451-95-8 ]

References: [1]Bioorganic and Medicinal Chemistry,2010,vol. 18,p. 2777 - 2784.

22
[ 20358-03-6 ]
2-(4-methyl-2-oxo-2H-chromen-7-yloxy)-N-(5-bromobenzo[d]thiazol-2-yl)acetamide [ No CAS ]

References: [1]Asian Journal of Chemistry,2011,vol. 23,p. 3969 - 3974.

23
[ 333-20-0 ]
[ 591-19-5 ]
[ 20358-03-6 ]