4-BROMO-2,5-DIMETHYLANILINE

Into a lOO-mL 3-necked round-bottom flask under N2 atmosphere, was placed 4- bromo-2, 5-dimethylaniline (2.5 g, 12.72 mmol, 1.5 equiv), Et2N (1.3 g, 12.72 mmol, 1.5 equiv), DCM (25 mL). 4-(2-(Benzyloxy)ethoxy)-l -methyl- 1 H-pyrazole-5 -carbonyl chloride_(2.5 g, 8.48 mmol, 1 equiv), prepared as described in Example 1, in 25 mL of DCM was added dropwise at 0 C. The resulting solution was stirred for 2 h at 0 C. The resulting mixture was concentrated under vacuum and the crude product was purified by re-crystallization from MeOH to give (3.78 g, 97.23%) of the title compound as a yellow solid. LC-MS: (ES, m/z) [M+H]+ 458.Into a 100-mL 3-necked round-bottom flask under N2 atmosphere, was placed 4- bromo-2, 5-dimethylaniline (2.5 g, 12.72 mmol, 1.5 equiv), EtiN (1.3 g, 12.72 mmol, 1.5 equiv), DCM (25 mL). 4-(2-(Benzyloxy)ethoxy)-l-methyl-lH-pyrazole-5-carbonyl chloride (2.5 g, 8.48 mmol, 1 equiv), prepared as described in Example 1, in 25 mL of DCM was added dropwise at 0 C. The resulting solution was stirred for 2 h at 0 C. The resulting mixture was concentrated under vacuum and the crude product was purified by re crystallization from MeOH to give (3.78 g, 97.23%) of the title compound as a yellow solid. LC-MS: (ES, m/z): [M+H]+ 458.Into a 25 -mL 3 -necked round-bottom flask under N2 atmosphere, was placed 4- allyl-l-methyl-lH-pyrazole-5-carboxylic acid (0.843 g, 5.07 mmol, 1 equiv), 4-bromo-2, 5- dimethylaniline (1.0 g, 5.00 mmol, 0.99 equiv), HATU (2.9 g, 7.63 mmol, 1 50 equiv), DIEA (1.3 g, 10.15 mmol, 2 equiv) and DMF (10 mL). The resulting solution was stirred overnight at room temperature. The reaction was then quenched with water and the resulting solution was extracted with ethyl acetate. The combined organic layer was concentrated under reduced pressure. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 : 10) to give 1.2 g (67.93%) of title compound as a white solid. LC- MS: (ES, m/z): [M+H]+ 348.Into a 25-mL 3-necked round-bottom flask under N2 atmosphere, was placed 4-allyl- 1 - methyl- 1 H-pyrazole-5 -carboxylic acid (0.843 g, 5.07 mmol, 1 equiv), 4-bromo-2, 5- dimethylaniline (1.0 g, 5.00 mmol, 0.99 equiv), HATU (2.9 g, 7.63 mmol, 1.50 equiv), DIEA (1.3 g, 10.15 mmol, 2 equiv) and DMF (10 mL). The resulting solution was stirred overnight at room temperature. The reaction was then quenched with water and the resulting solution was extracted with ethyl acetate. The combined organic layer was concentrated under reduced pressure. The residue was applied onto a silica gel column and eluted with ethyl acetate/petroleum ether (1 : 10) to give 1.2 g (67.93%) oftitle compound as a white solid. LC-MS: (ES, m/z): [M+H]+ 348.Into a 100 mL 3-necked round-bottom flask was added 4-bromo-2, 5- dimethylaniline (3.3 g, 16.50 mmol, 1 equiv), DCM (50 mL), and Et3N (3.3 g, 32.61 mmol, 1.98 equiv). To the above mixture l-(2-(benzyloxy)ethyl)-4-methyl-lH-pyrazole-5-carbonyl chloride (4.6 g, 16.50 mmol, 1 equiv) in 20 mL of DCM was added dropwise at 0 C. The resulting mixture was stirred for additional 1 h at room temperature. The reaction mixture was quenched with water and the aqueous layer was extracted with CH2CI2. The combined organic layer was dried over anhydrous sodium sulfate and concentrated under vacuum. The crude product was re-crystallized from MeOH (50 mL) to afford (5.4 g, 73.97%) of the title compound as a white solid. LC-MS: (ES , m/z): [M+H]+ 442.Into a 100 mL 3-necked round-bottom flask was added

Molecular Weight:200.08
XLogP3:2.7
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:198.99966
Monoisotopic Mass:198.99966
Topological Polar Surface Area:26
Heavy Atom Count:10
Complexity:116
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes