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Chemical Structure| 824403-26-1 Chemical Structure| 824403-26-1

Structure of 824403-26-1

Chemical Structure| 824403-26-1

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Product Details of [ 824403-26-1 ]

CAS No. :824403-26-1
Formula : C7H3BrClNS
M.W : 248.53
SMILES Code : ClC1=NC2=CC(Br)=CC=C2S1
MDL No. :MFCD09749227
InChI Key :CQHUAYKIQCBOKY-UHFFFAOYSA-N
Pubchem ID :20251269

Safety of [ 824403-26-1 ]

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

Application In Synthesis of [ 824403-26-1 ]

* 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 [ 824403-26-1 ]

[ 824403-26-1 ] Synthesis Path-Downstream   1~8

  • 2
  • [ 824403-26-1 ]
  • (R)-1-(pyrrolidin-3-yl)piperidine dihydrochloride [ No CAS ]
  • [ 1161730-99-9 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 100.0℃; for 15.0h;Product distribution / selectivity; A stirred mixture of 2-chloro-5-bromobenzothiazole (CAS No.824403-26-1, catalog No.20284, Daxian Chemical Institute Ltd., No.179, 10169 New Hampshire Ave., Silver Spring, Md. 20903, 2.485 g, 0.0100 mole), (R)-1-(pyrrolidin-3-yl)piperidine dihydrochloride (Reference Example 5c, 2.73 g, 0.0120 mole), and potassium carbonate (6.00 g, 0.04438 mole) in N,N-dimethylformamide (15 mL) is heated to 100 C. with an oil bath for 15 hours. The reaction mixture is cooled to room temperature then poured into water (300 mL). The resulting precipitate is collected by filtration and the filter cake is rinsed with water (600 mL). The solid is dissolved in dichloromethane and the solution is dried (MgSO4) and filtered. The filtrate is concentrated under reduced pressure to give a solid that is crystallized from hot ethyl acetate to give (R)-5-bromo-2-(3-(piperidin-1-yl)pyrrolidin-1-yl)benzo[d]thiazole.
  • 3
  • [ 824403-26-1 ]
  • [ 60979-25-1 ]
  • 3-((5-bromobenzo[d]thiazol-2-yl)amino)-4-methoxybenzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
In phenol; at 100.0℃; Intermediate 1: Step b3-((5-Bromobenzo [d] thiazol-2-yl)amino)-4-methoxybenzonitrileCommercially available <strong>[824403-26-1]5-bromo-2-chlorobenzo[d]thiazole</strong> (2.0 g, 8.05 mmol) in phenol (4 g) was treated with 3-amino-4-methoxybenzonitrile (1.31 g, 8.85 mmol, intermediate 1, step a). The mixture was heated to 100 C overnight. The resulting red-brown solution was cooled to room temperature. To the solid formed upon cooling was added EtOAc and saturated aqueous NaHCC solution. The mixture was stirred for 1 h to dissolve the solid. The aqueous layer was separated out. The organic layer was washed with IN NaOH solution for 5 times to get rid of phenol. The organic layer was dried (MgS04) and concentrated in vacuo to obtain the title compound as a solid.
  • 4
  • bromo(cyclopropyl)zinc [ No CAS ]
  • [ 824403-26-1 ]
  • 5-bromo-2-cyclopropylbenzo[d]thiazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
88% With tetrakis(triphenylphosphine) palladium(0); In tetrahydrofuran; at 60.0℃; for 18.25h;Inert atmosphere; Step 1 : 5-Bromo-2-cyclopropylbenzo[ |thiazole [00332] To a solution of <strong>[824403-26-1]5-bromo-2-chlorobenzo[d]thiazole</strong> (0.50 g, 2.02 mmol) and Pd(PPh3)4 (70 mg, 0.06 mmol) in THF (5 mL) was added dropwise cyclopropyl zinc bromide (0.5 M in THF, 4.0 mL, 2.02 mmol), over 15 min. The reaction mixture heated to 60 C under N2 for 1 8 h. The reaction mixture was cooled to 0 C and quenched with saturated sodium hydrogen carbonate solution (1 0 mL). The corresponding solution was partitioned with ethyl acetate (50 mL), washed with saturated sodium hydrogen carbonate solution (30 mL), dried over MgS04 and concentrated to give an orange solid. The crude reaction material was purified by flash silica chromatography (gradient elution /'-hex to 50% EtOAc in /-hex) to give the title compound as a pale yellow solid (0.45 g, 88%). LCMS (ES+) consistent with target (M+H)+.
  • 5
  • [ 824403-26-1 ]
  • [ 75-31-0 ]
  • C10H11BrN2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
79% In ethanol; at 100.0℃; for 1.0h;Microwave irradiation; To a solution of <strong>[824403-26-1]5-bromo-2-chlorobenzo[d]thiazole</strong> (0.87 g, 3.5 mmol) in ethanol (12 mL) was added isopropylamine solution (1.5 mL) and the mixture was heated for 60 minutes using a Biotage microwave oven at 100C. The reaction mixture was cooled to room temperature. The solvent was removed, the crude product was dissolved in dichlormethane (150 mL) and washed with 1 M NaOH solution, water and brine and dried over Na2S04. The solvent was removed under reduced pressure to give a crude product, which was purified on a silica gel column using an EtOAc and heptane gradient (20/80 => 50/50) to afford the title compound as a solid (0.75 g, 79 %). (0516) 1H-NMR (400 MHz, Chloroform-d) d = 7.67 (d, J = 1.9 Hz, 1 H), 7.43 (d, J = 8.5 Hz, 1 H), 7.19 (dd, J = 8.3, 1.9 Hz, 1 H), 5.47 (s, 1 H), 4.04 - 3.79 (m, 1 H), 1.34 (d, J = 6.5 Hz, 6H).
  • 6
  • [ 824403-26-1 ]
  • [ 74-89-5 ]
  • 5-bromo-N-methyl-1,3-benzothiazol-2-amine [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% In ethanol; at 100.0℃; for 1.5h;Microwave irradiation; To a solution of <strong>[824403-26-1]5-bromo-2-chlorobenzo[d]thiazole</strong> (0.9 g, 3.62 mmol) in ethanol (12 mL) was added 4M methylamine solution (1 mL) and the mixture was heated for 90 minutes using a Biotage microwave oven at 100C. The reaction mixture was cooled to room temperature. The solvent was removed, the crude product was purified on a silica gel column using an EtOAc and heptane gradient (20/80 => 50/50) to afford the title compound as a solid (0.57 g, 65 %). (0511) 1H-NMR (400 MHz, Chloroform-c/) d = 7.68 (t, J = 2.0 Hz, 1 H), 7.46 (d, J = 8.3 Hz, 1 H), 7.22 (dd, J = 8.4, 1.9 Hz, 1 H), 5.90 (s, 1 H), 3.13 (s, 3H).
65% In ethanol; at 150.0℃; for 0.75h;Microwave irradiation; To a solution of 5-bromo-2-chlorobenzo[cf]thiazole (0.9 g, 3.62 mmol) in ethanol (12 ml), was added 4 M methyl amine solution (1 ml_) and the reaction mixture was heated at 150 C for 45 min using a Biotage microwave. The reaction mixture was cooled to room temperature. The solvent was removed under reduced pressure, and the crude reaction mixture was purified by flash column chromatography using hexane: ethyl acetate (50:50) to afford the title compound as a solid (0.57 g, 65%).1H-NMR (400 MHz, CDCI3) d = 7.68 (t, J = 2.0 Hz, 1 H), 7.46 (d, J = 8.3 Hz, 1 H), 7.29 (d, J = 0.7 Hz, 1 H), 7.22 (dd, J = 8.4, 1.9 Hz, 1 H), 5.90 (s, 1 H), 3.13 (s, 3H).
  • 7
  • [ 824403-26-1 ]
  • C22H23FN4S [ No CAS ]
  • 8
  • [ 824403-26-1 ]
  • C20H19FN4S [ No CAS ]
 

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