4-BROMO-THIAZOL-2-YLAMINE

To a solution of To a suspension of intermediate 1 (1.0 g, 3.7 mmol) in DCE (10 mL) was added SOCb (2.7 mL, 37 mmol) and the reaction mixture was heated to 50 C. After 1 h, the solvents were removed under reduced pressure and THF (10 ml), 4-bromothiazol-2- amine (0.70 g, 4.0 mmol), and DIEA (2 mL, 11 mmol) were added. After 24 h, the solvents were removed under reduced pressure and residue was purified via silica gel chromatography to afford (1.1 g, 71 % yield) of N-(4-bromothiazol-2-yl)-2-(4-((3- cyanopyridin-2-yl)oxy)-3-fluorophenyl)acetamide as a brown solid. LCMS(ESI) m/z: 432.7-434.7 (M+H).+ MR (400 MHz, CD3OD) delta 8.32 (dd, 7=5.0, 1.9 Hz, 1H), 8.27 (dd, 7=7.6, 1.9 Hz, 1H), 7.39 - 7.25 (m, 4H), 7.08 (s, 1H), 3.90 (s, 2H).Di-/er/-butyl dicarbonate (2.43 g, 11.17 mmol) was added to a mixture of To a stirred solution of (2S, 4R)-1-(tert-butoxycarbonyl)-4-fluoropyrrolidine-2-carboxylic acid (250 mg, 1.07 mmole) in 10 mL of CH2Cl2, was added 1-methyl imidazole (0.21 mL, 2.5 equiv.) at 0-5 C. under nitrogen atmosphere. The reaction mixture was stirred for 10 min at 0-5 C. and then added methane sulfonyl chloride (0.1 mL, 1.2 equiv) at the same temperature. It was stirred for 1 h at 0-50 C. Then 3-pyridyl boronic acid (20mmole), 2-Amino-4-bromo - thiazole (20 mmol) dissolved in Dioxane - water(1:1, 70), then added Potassium carbonate (50 mmol) and replaced three times with argongas . the again add Bis (triphenylphosphine) palladium (II) dichloride (1mmol) and the reaction was heatedat reflux for 5h. Cooling, the solvent was distilled off under reducedpressure, the residue was dissolved with methylene chloridethen it was driedover anhydrous sodium sulfate and by column chromatography to give 4-(3-pyridyl) -2-aminothiazole 2.5g.Example 21: Intermediate 23- -(4-bromothiazol-2-yl)acetamide [0266] A solution of Example 347 2-(4-Furan-2-yl-thiazol-2-ylcarbamoyl)-pyrrolidine-1-carboxylic acid benzyl ester (Compound 5347) 4-Furan-2-yl-thiazol-2-ylamine

4-Bromo-2-thiazolamine is used in the preparation of coumarin derivatives with antimicrobial properties.

Molecular Weight:179.04
XLogP3:1.6
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:177.92003
Monoisotopic Mass:177.92003
Topological Polar Surface Area:67.2
Heavy Atom Count:7
Complexity:70
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes