4-Amino-3-bromobenzoic acid

White to light yellow crystal powder

4-Amino-benzoic acid (100 mmol) was dissolved in DMF (50 mL) and iV-bromosuccinimide(100 mmol) was added. Stirred at ambient temperature for 18h, the reaction mixture was then poured into water (100 mL). The product was removed by filtration, washed with water and dried in vacuo to give 4-amino-3-bromo-benzoic acid.Yield: 70percentIH NMR (D4-Amino-benzoic acid (100 mmol) was dissolved in DMF (50 mL) and N-bromo- succinimide (100 mmol) was added. Stirred at ambient temperature for 18h, the reaction mixture was then poured into water (100 mL). The product was removed by filtration, washed with water and dried in vacuo. Yield: 70percent 1H NMR (D6-DMSO) : 6.10 (s, 2H); 6.78 (d, 1H); 7.63 (dd, 1H); 7.89 (d, 1H) ; 12.39 (br s, 1H).4-Amino-benzoic acid (100 mmol) was dissolved in DMF (100 mL) and N-bromo succinimide (100 mmol) was added portion wise. The orange reaction mixture was stirred over night at ambient temperature, then poured into water. The product was collected by filtration and re-crystallized from MeOH. Yield: 65percent 1H NMR (D6-DMSO) : 6.09 (s, 2H); 6.81 (d, 1H); 7.13 (dd, 1H); 7.89 (d, 1H) ; 12.37 (br, 1H).General procedure: To a round bottom flask was added 5 mmol of acetophenone, 0.5 mmol of 2-methylpyridine nitrate and 5.5 mmol of 40 wtpercent HBr, 60 ° C under the open flask stir reaction 6h, The yield of α-bromoacetophenone was 95percent The product was isolated by silica gel column chromatography (ethyl acetate / boiling point 60-90 ° C petroleum ether) at 200-300 mesh, The isolated yield was 88percent.SynthesisPeptidomimetics 37-44 were synthesized via solid phase peptide synthesis, using Suzuki couplings employing various boronic acids and aryl bromides. Intermediates display hydrophobic substituents from the aromatic spacer (Abz). The simple quinazoline scaffolds derived from commercially available starting materials. The synthesis of the quinazolines cores 45a-b was accomplished by the cyclization of 4-nitroanthranilic acid by the reaction with sodium isocyanate or cyclization employing a carbon dioxide atmosphere with catalytic DBU (1 , 8-diazabicyclo[5.4.0]undec-7-ene) from 4- and 5-nitro precursors respectively Figure 10. Alkylation was followed by reduction of the nitro group followed by coupling with A- nitrobenzoyl chloride via anilide formation to provide 48a-b. Reduction to the aniline, coupling with AcArg(Pmc)-OH, and deprotection of the guanidine protecting group afforded 50a-b.A convergent synthesis using methyl-4-amino-2-bromobenzoate or methyl-4-aminobenzoate and 4-nitroaniline created non-peptidic inhibitors 56aa-ci, as seen in Figure 13. Suzuki coupling of the bromoaniline with the corresponding boronic acid, employing PdCI

Molecular Weight:216.03
XLogP3:1.5
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Rotatable Bond Count:1
Exact Mass:214.95819
Monoisotopic Mass:214.95819
Topological Polar Surface Area:63.3
Heavy Atom Count:11
Complexity:163
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes