408328-13-2|2,6-Dibromobenzothiazole| Ambeed

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Quality Control of [ 408328-13-2 ] Purity: 95% SDS Specification

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Product Details of [ 408328-13-2 ]

CAS No. :	408328-13-2
Formula :	C₇H₃Br₂NS
M.W :	292.98
SMILES Code :	BrC1=NC2=C(S1)C=C(C=C2)Br
MDL No. :	MFCD07783783
InChI Key :	LQVHXPZEBKDACR-UHFFFAOYSA-N
Pubchem ID :	24728904

Safety of [ 408328-13-2 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301
Precautionary Statements:	P301+P310
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of [ 408328-13-2 ]

* 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.

Downstream synthetic route of [ 408328-13-2 ]

[ 408328-13-2 ] Synthesis Path-Downstream 1~33

1
[ 408328-13-2 ]
[ 62266-82-4 ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.

3
[ 408328-13-2 ]
2-methoxy-benzothiazol-7-ylamine [ No CAS ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.
[2]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.

4
[ 408328-13-2 ]
6-bromo-2-methoxy-benzothiazol-7-ylamine [ No CAS ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.
[2]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.

5
[ 408328-13-2 ]
6-bromo-7-nitro-3<i>H</i>-benzothiazol-2-one [ No CAS ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.
[2]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.
[3]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.

6
[ 408328-13-2 ]
[ 408314-98-7 ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.
[2]Journal of Organic Chemistry,1953,vol. 18,p. 1092,1099.

7
[ 408328-13-2 ]
[ 163105-89-3 ]
6-bromo-2-(6-methoxypyridin-3-yl)-1,3-benzothiazole [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With sodium carbonate;dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH2Cl2; In tetrahydrofuran; water; at 140℃; for 0.166667h;Microwave irradiation;	A mixture of 2,6-dibromo-benzothiazole (0.29 g, 1.0 mmol), 2-methoxy-5-pyridineboronic acid (0.17 g, 1.1 mmol), Pd(dppf)Cl2*DCM (41 mg, 0.05 mmol) and sodium carbonate (0.382 g, 3.6 mmol) in THF/water (9:1, 4 niL) was heated at 140 C for 10 minutes in a microwave reactor. The reaction mixture was thereafter filtered through a plug of silica using DCM as eluent. The filtrate was concentrated and the crude product was purified by flash column chromatography (10% ethyl acetate in heptane), followed by recrystallization from ethyl acetate, to give the title compound (61 mg) as a solid. 1H NMR (CHLOROFORM-^ δ 8.83 (d, 2 H) 8.27 (dd, 1 H) 8.03 (d, 1 H) 7.90 (d, 1 H) 7.60 (dd, 1 H) 6.87 (d, 1 H) 4.03 (s, 3 H); MS m/z (M+H) 321.

References: [1]Patent: WO2007/86800,2007,A1 .Location in patent: Page/Page column 73.

8
[ 15864-32-1 ]
[ 408328-13-2 ]

Yield	Reaction Conditions	Operation in experiment
87%	With copper(ll) bromide; isopentyl nitrite; In acetonitrile; at 0℃; for 1h;	General procedure: To a mixture of 6-bromobenzo[d]thiazol-2-amine (470 mg, 2.01 mmol) and CuBr2 (760 mg, 3.42 mmol) in MeCN (10 mL) at 0 C, was added iso-pentyl nitrite (280 mg, 2.41 mmol) dropwise. The reaction mixture was stirred at 0 C for 1 h and then H2O (100 mL) was added. The resulting precipitate was filtered and dried in vacuum to give the title compound (515 mg, 87%) as a brown solid.
77%	With tert.-butylnitrite; copper(ll) bromide; In acetonitrile; at 65℃; for 3h;	6- bromobenzo[d]thiazol-2-amine (2.50 g; 14.1 mmol) was dissolved in 70 mL acetonitrile. t- Butylnitrite (1.7 mL; 14 mmol) was added slowly. Cu(II)Br (2.5 g; 17.6 mmol) was added portion-wise through a funnel. The reaction was monitored by HPLC. After 3 hours, ethyl acetate (250 mL) was added, and the mixture was filtered through celite. The organic layer was washed with brine twice (150 mL each). The organic layer was dried over MgSO4. After filtration, the solvent was removed. The residual was dissolved in 50 mL CH2Cl2, and 2 g of silica gel was added. After drying, the silica gel loaded on a silica gel cake in hexane. The product was eluted with 5% ethyl acetate and 95% hexane. A yellowish band was collected. The solvent was removed to afford the product (2.4 g, 77 % yield). MS: 291.84 [M++1].
		Compound 4a (0.8 g, 3.5 mmol) was mixed under intensive stirring with 85% phosphoric acid (8 ml) at 50 C. The solution was cooled to -20 C and a solution of sodium nitrite (0.29 g, 4.2 mmol) in water (2 ml) was added slowly to keep the temperature below -10 C. After stirring for 1 h, the resulting diazonium salt was poured into a solution of active copper(I) bromide (0.65 g, 4.5 mmol) in 48% HBr (5 ml). The mixture was intensively stirred for 1 h at room temperature, at 40 C for 2 h and then at room temperature overnight, poured into ice-water (100 ml) then extracted with ethyl acetate (100 ml * 1, 50 ml * 2). The organic layer was collected and washed with saturated Na2CO3, saturated salt water, then dried over anhydrous Na2SO4 and filtered. Then ethyl acetate was evaporated off to give 7a as brown crude product which was used for the next step directly.

References: [1]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3665 - 3670.
[2]Patent: WO2020/261294,2020,A1 .Location in patent: Page/Page column 61-62.
[3]Journal of Organic Chemistry,2010,vol. 75,p. 3053 - 3068.
[4]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3739 - 3748.
[5]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6477 - 6485.

9
[ 408328-13-2 ]
C₁₄H₁₃BrO₂S [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 1039 - 1044.

10
[ 408328-13-2 ]
N-({1-[4-(4-bromo-thiophen-2-yl)-4-hydroxy-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide [ No CAS ]
N-({1-[4-(4-bromo-thiophen-2-yl)-4-hydroxy-cyclohexyl]-azetidin-3-ylcarbamoyl}-methyl)-3-trifluoromethyl-benzamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 1039 - 1044.

11
[ 408328-13-2 ]
N-[1-(4-benzothiazol-2-yl-4-hydroxy-cyclohexyl)-azetidin-3-ylcarbamoyl]-methyl}-3-trifluoromethyl-benzamide [ No CAS ]

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 1039 - 1044.

12
[ 4746-97-8 ]
[ 408328-13-2 ]
[ 1228652-52-5 ]

References: [1]ACS Medicinal Chemistry Letters,2012,vol. 3,p. 1039 - 1044.

13
[ 408328-13-2 ]
[ 1616589-55-9 ]

References: [1]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3739 - 3748.

14
[ 408328-13-2 ]
[ 765-30-0 ]
[ 1177325-80-2 ]

Yield	Reaction Conditions	Operation in experiment
68%	In 1,4-dioxane; for 6h;Inert atmosphere;	<strong>[408328-13-2]2,6-dibromobenzo[d]thiazole</strong> (1.0 g, 3.4 mmol) was suspended in 1,4-dioxane (10 ml), and added cyclopropylamine (3.6 ml, 51.0 mmol). The resultant mixture is stirred under nitrogen for 6 hours and cool to room temperature. On completion of reaction following a TLC examination, the reaction mixture was extracted with ethyl acetate and washed with brine. The solvent was removed. The crude product obtained was purified by flash chromatography (Hex:AcOEt 1:1) to afford 6-bromo-N-cyclopropylbenzo[d]thiazol-2-amine (0.630 mg, 68 % yield) as pale yellow solid. MS: 268.97 [M++1].
56%	In 1,4-dioxane; at 80℃; for 12h;	General procedure: A mixture of <strong>[408328-13-2]2,6-dibromobenzo[d]thiazole</strong> (293 mg, 1.00 mmol) and corresponding amine (3 eq) in1,4-dioxane (3 mL) was heated to 80 C overnight. After cooling to room temperature, the solvent was removed by vacuum and the resulting residue was dissolved in ethyl acetate (50 mL), and washed with brine (10 mL * 3). The organic layer was dried over Na2SO4, and concentrated in vacuum to give the desired product.
0.44 g	In 1,4-dioxane; for 6h;Inert atmosphere; Reflux;	Compound 7a (1.0 g, 3.4 mmol) was suspended in 1,4-dioxane (10 ml), and cyclopropylamine (3.6 ml, 51.0 mmol) was added. The resulting mixture was heated to reflux under nitrogen for 6 h, cooled to room temperature. The solvent was evaporated off to give crude product which was purified through column chromatograph to give 8a (0.44 g, 48%) as off-white solid. Mp: 183.0-184.0 C; 1H NMR (DMSO-d6): δ 8.49 (s, 1H, NH), 7.97 (d, J = 2.0 Hz, 1H, Ar-H), 7.37 (d, J = 8.8 Hz, 1H, Ar-H), 7.33 (m, 1H, Ar-H), 2.68 (m, 1H, CH), 0.77 (m, 2H, CH2), 0.57 (m, 2H, CH2). ESI-HRMS m/z: calcd for C10H10BrN2S [M+H]+: 268.9748; found 268.9749.

References: [1]Patent: WO2020/261294,2020,A1 .Location in patent: Page/Page column 61-62.
[2]Bioorganic and Medicinal Chemistry Letters,2015,vol. 25,p. 3665 - 3670.
[3]Bioorganic and Medicinal Chemistry,2014,vol. 22,p. 3739 - 3748.
[4]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 6477 - 6485.

15
[ 408328-13-2 ]
N-(2-chloro-5-(2-(cyclopropylamino)benzo[d]thiazol-6-yl)pyridin-3-yl)benzamide [ No CAS ]