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Chemical Structure| 15864-32-1 Chemical Structure| 15864-32-1
Chemical Structure| 15864-32-1

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CAS No.: 15864-32-1

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Product Citations

Walczak, Juliusz Maksymilian ; Iwaszkiewicz-Grzes, Dorota ; Ziomkowska, Michalina ; Sliwka-Kaszynska, Magdalena ; Dasko, Mateusz ; Trzonkowski, Piotr , et al.

Abstract: The group of 18 new amide derivatives of mycophenolic acid (MPA) and selected heterocyclic amines was synthesised as potential immunosuppressive agents functioning as inosine-5′-monophosphate dehydrogenase (IMPDH) uncompetitive inhibitors. The synthesis of 14 of them employed uronium-type activating system (TBTU/HOBt/DIPEA) while 4 of them concerned phosphonic acid anhydride method (T3P/Py) facilitating amides to be obtained in moderate to excellent yields without the need of phenolic group protection. Most of optimised protocols did not require complicated reaction work-ups, including chromatographic, solvent-consuming methods. The biological activity assay was performed on the T-Jurkat cell line and peripheral mononuclear blood cells (PBMCs) which are both dedicated for antiproliferative activity determination. Each of designed derivatives was characterised by reduced cytotoxicity and benzoxazole analogue (A2) revealed the most promising activity. Subsequently, an observed structure-activity relationship was discussed.

Keywords: Mycophenolic acid ; amide derivatives ; heterocycles ; benzoxazole ; IMPDH inhibition

Alternative Products

Product Details of 2-Amino-6-bromobenzothiazole

CAS No. :15864-32-1
Formula : C7H5BrN2S
M.W : 229.10
SMILES Code : C1=C(C=C2C(=C1)N=C(S2)N)Br
MDL No. :MFCD00152229
InChI Key :VZEBSJIOUMDNLY-UHFFFAOYSA-N
Pubchem ID :85149

Safety of 2-Amino-6-bromobenzothiazole

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

Application In Synthesis of 2-Amino-6-bromobenzothiazole

* 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 [ 15864-32-1 ]

[ 15864-32-1 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 15864-32-1 ]
  • [ 408328-13-2 ]
YieldReaction ConditionsOperation 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.
  • 2
  • [ 15864-32-1 ]
  • [ 885069-14-7 ]
  • 3
  • [ 15864-32-1 ]
  • [ 73183-34-3 ]
  • [ 885069-14-7 ]
  • 4
  • [ 15864-32-1 ]
  • [ 612845-44-0 ]
  • C14H13N3OS [ No CAS ]
  • 5
  • [ 123-91-1 ]
  • [ 72287-26-4 ]
  • [ 15864-32-1 ]
  • [ 24424-99-5 ]
  • [ 96042-30-7 ]
  • [ 564483-18-7 ]
  • [ 1244059-50-4 ]
YieldReaction ConditionsOperation in experiment
With dmap; potassium acetate; Step 1: tert-Butyl (6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzo[d]thiazol-2-yl)carbamate A 100 mL flask charged with 2-amino-6-bromobenzothiazole (2.52 g, 10.77 mmol), bis(pinacolato)diboron (5.45 g, 21.24 mmol), potassium acetate (3.28 g, 33.09 mmol), 2-(dicyclohexylphosphino)-2',4',6'-triisopropylbiphenyl (212.2 mg, 0.436 mmol), and tris(dibenylideneacetone)dipalladium chloroform complex (117.9 mg, 0.110 mmol) was evacuated and backfilled with nitrogen. 1,4-Dioxane (20.0 mL, 233 mmol) was added and the reaction mixture stirred under a nitrogen balloon at 100° C. for 1 h. To the reaction was then added [1,1'-bis(diphenylphosphino)ferrocene]palladium(II) chloride, complex with DCM (1:1) (285.9 mg, 0.350 mmol). After an additional 17 h the reaction mixture was cooled to room temperature, filtered through celite, rinsing with ethyl acetate, and then evaporated to dry on celite. The crude product was purified via flash chromatography on silica gel (80 g silica, solvent gradient: 0-100percent isopropyl acetate in heptanes) to yield 2.85 g. Of this material, 2.64 g was combined with di-tert-butyl dicarbonate (2.58 g, 11.45 mmol), 4-dimethylaminopyridine (79.9 mg, 0.654 mmol) and DCM (20.0 mL, 312 mmol) and stirred at room temperature for 2 h. The mixture was evaporated in vacuo and the crude product was purified via flash chromatography on silica gel (40 g silica, solvent gradient: 0-50percent ethyl acetate in heptane) to yield 2.24 g of the title compound. LCMS (ESI): [M+H]+=377.
 

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