3-Amino-6-[4-(methylsulfonyl)phenyl]-N-phenyl-2-pyrazinecarboxamide

Bright Yellow Solid

3-amino-6-(4-methylsulfonylphenyl)-N-phenyl-2-pyrazinecarboxamide is an aromatic amide.

A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.1 14 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 μL, 5.1 14 mmol), aniline (476.2 mg, 465.9 μL, 5.1 14 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) were stirred in DME (18.75 mL) at 120 °C for 18 hours. After this time water was added and the resultant solid collected by filtration. The solid was triturated with acetone and dried to give the desired product (1.335g, 71percent Yield). 1H NMR (400.0 MHz, DMSO) d 3.28 (s, 3H), 7.18 (t, J = 7.3 Hz, I H), 7.41 (t, J = 7.8 Hz, 2H), 7.82 (d, J = 7.9 Hz, 2H), 7.89 (s, 2H), 8.01 (d, J = 8.4 Hz, 2H), 8.51 (d, J = 8.4 Hz, 2H), 9.04 (s, 1H) andlψ.47 (s, I H) ppm; MS (ESStep 4: 3-Amino-6-(4-(methylsulfonyl)phenyl)-iV-phenylpyrazine-2-carboxamide[00144] A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.114 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 μ, 5.114 mmol), aniline (476.2 mg, 465.9 μ, 5.114 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) was stirred in DME (18.75 mL) at 120 °C for 18 hours. After this time water was added and the resultant solid collected by filtration and triturated with acetone to give the desired product (1.88g, 71percent Yield). 3/4 NMR (400.0 MHz, DMSO) δ 10.47 (s, 1H), 9.04 (s, 1H), 8.51 (d, J = 8.4 Hz, 2H), 8.01 (d, J = 8.4 Hz, 2H), 7.89 (s, 2H), 7.82 (d, J = 7.9 Hz, 2H), 7.41 (t, J = 7.8 Hz, 2H), 7.18 (t, J = 7.3 Hz, 1H) and 3.28 (s, 3H) ppm; MS (ESA mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.1 14 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 μL, 5.1 14 mmol), aniline (476.2 mg, 465.9 μL, 5.1 14 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) were stirred in DME (18.75 mL) at 120 °C for 18 hours. After this time water was added and the resultant solid collected by filtration. The solid was triturated with acetone and dried to give the desired product (1.335g, 71percent Yield). 1H NMR (400.0 MHz, DMSO) d 3.28 (s, 3H), 7.18 (t, J = 7.3 Hz, I H), 7.41 (t, J = 7.8 Hz, 2H), 7.82 (d, J = 7.9 Hz, 2H), 7.89 (s, 2H), 8.01 (d, J = 8.4 Hz, 2H), 8.51 (d, J = 8.4 Hz, 2H), 9.04 (s, 1H) andlψ.47 (s, I H) ppm; MS (ESStep 4: 3-Amino-6-(4-(methylsulfonyl)phenyl)-iV-phenylpyrazine-2-carboxamide[00144] A mixture of 3-amino-6-(4-methylsulfonylphenyl)pyrazine-2-carboxylic acid (1.5 g, 5.114 mmol), diethoxyphosphorylformonitrile (926.8 mg, 849.5 μ, 5.114 mmol), aniline (476.2 mg, 465.9 μ, 5.114 mmol) and triethylamine (1.035 g, 1.426 mL, 10.23 mmol) was stirred in DME (18.75 mL) at 120 °C for 18 hours. After this time water was added and the resultant solid collected by filtration and triturated with acetone to give the desired product (1.88g, 71percent Yield). 3/4 NMR (400.0 MHz, DMSO) δ 10.47 (s, 1H), 9.04 (s, 1H), 8.51 (d, J = 8.4 Hz, 2H), 8.01 (d, J = 8.4 Hz, 2H), 7.89 (s, 2H), 7.82 (d, J = 7.9 Hz, 2H), 7.41 (t, J = 7.8 Hz, 2H), 7.18 (t, J = 7.3 Hz, 1H) and 3.28 (s, 3H) ppm; MS (ES

VE 821 is a potent and selective inhibitor of DNA damage response kinase, ATR. VE 821 functions to disrupt DNA damage repair system of tumor cells, limiting their abilities for further growth.

Molecular Weight:368.4
XLogP3:2.1
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:6
Rotatable Bond Count:4
Exact Mass:368.09431156
Monoisotopic Mass:368.09431156
Topological Polar Surface Area:123
Heavy Atom Count:26
Complexity:578
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes