e.g. Filippa Pettersson or Cancer Res. 75(6) , 1102-12, (2015) or 10.1002/anie.201600521

Synthesis and characterization of masked aminopyrazolecarboxylic acid synthons

…, BF Cain, WA Denny, JS Buckleton…

Index: Lee, Ho H.; Cain, Bruce F.; Denny, William A.; Buckleton, John S.; Clark, George R. Journal of Organic Chemistry, 1989 , vol. 54, # 2 p. 428 - 431

Full Text: HTML

Citation Number: 57

Abstract

The synthesis of the masked aminopyrazolecarboxylic acid synthons (1 la, b and 12a, b) from pyrazole-3, 5-dicarboxylic acid (6) and the determination of their structures by X-ray crystallography are detailed. The compounds are useful for the synthesis of polypyrazolecarboxamides analogous to the DNA minor groove binding antibiotics distamycin A and netropsin.

3,5-Dimethylpyrazole Structure

3,5-Dimethylpyrazole

~%

1H-Pyrazole-5-carboxylic acid, 3-(chlorocarbonyl)-1-methyl-, methyl ester (9CI) Structure

1H-Pyrazole-5-c...

3,5-Pyrazoledicarboxylic acid monohydrate Structure

3,5-Pyrazoledic...

~%

1H-Pyrazole-5-carboxylic acid, 3-(chlorocarbonyl)-1-methyl-, methyl ester (9CI) Structure

1H-Pyrazole-5-c...

1H-Pyrazole-3,5-dicarbonyldichloride(9CI) Structure

1H-Pyrazole-3,5...

~%

1H-Pyrazole-5-carboxylic acid, 3-(chlorocarbonyl)-1-methyl-, methyl ester (9CI) Structure

1H-Pyrazole-5-c...

1,3,5-TRIMETHYL-PYRAZOLE-3,5-DICARBOXYLATE Structure

1,3,5-TRIMETHYL...

~%

1H-Pyrazole-5-carboxylic acid, 3-(chlorocarbonyl)-1-methyl-, methyl ester (9CI) Structure

1H-Pyrazole-5-c...

methyl 2-methyl-5-(phenylmethoxycarbonylamino)pyrazole-3-carboxylate Structure

methyl 2-methyl...

~%

1H-Pyrazole-5-carboxylicacid,3-amino-1-methyl-(9CI) Structure

1H-Pyrazole-5-c...

1-methyl-3-benzyloxy-carbonylamino-pyrazole-5-carboxylic acid Structure

1-methyl-3-benz...

~%

1H-Pyrazole-5-carboxylicacid,3-amino-1-methyl-(9CI) Structure

1H-Pyrazole-5-c...

1,3,5-TRIMETHYL-PYRAZOLE-3,5-DICARBOXYLATE Structure

1,3,5-TRIMETHYL...

~68%

5-(methoxycarbonyl)-1-methyl-1H-pyrazole-3-carboxylic acid Structure

5-(methoxycarbo...

1,3,5-TRIMETHYL-PYRAZOLE-3,5-DICARBOXYLATE Structure

1,3,5-TRIMETHYL...

~%

methyl 2-methyl-5-(phenylmethoxycarbonylamino)pyrazole-3-carboxylate Structure

methyl 2-methyl...

5-(methoxycarbonyl)-1-methyl-1H-pyrazole-3-carboxylic acid Structure

5-(methoxycarbo...

~%

methyl 2-methyl-5-(phenylmethoxycarbonylamino)pyrazole-3-carboxylate Structure

methyl 2-methyl...

1H-Pyrazole-5-carboxylic acid, 3-(chlorocarbonyl)-1-methyl-, methyl ester (9CI) Structure

1H-Pyrazole-5-c...

~%

methyl 2-methyl-5-(phenylmethoxycarbonylamino)pyrazole-3-carboxylate Structure

methyl 2-methyl...

methyl 3-(azidocarbonyl)-1-methyl-1H-pyrazole-5-carboxylate Structure

methyl 3-(azido...

Benzyl alcohol Structure

~%

methyl 2-methyl-5-(phenylmethoxycarbonylamino)pyrazole-3-carboxylate Structure

methyl 2-methyl...

3,5-Dimethylpyrazole Structure

3,5-Dimethylpyrazole

~%

1H-Pyrazole-3,5-dicarbonyldichloride(9CI) Structure

1H-Pyrazole-3,5...

1,3,5-TRIMETHYL-PYRAZOLE-3,5-DICARBOXYLATE Structure

1,3,5-TRIMETHYL...

~87%

1-METHYL-1H-PYRAZOLE-3,5-DICARBOXYLIC ACID Structure

1-METHYL-1H-PYR...

1-METHYL-1H-PYRAZOLE-3,5-DICARBOXYLIC ACID 3-METHYL ESTER Structure

1-METHYL-1H-PYR...

3,5-Dimethylpyrazole Structure

3,5-Dimethylpyrazole

~%

1-METHYL-1H-PYRAZOLE-3,5-DICARBOXYLIC ACID 3-METHYL ESTER Structure

1-METHYL-1H-PYR...

3,5-Pyrazoledicarboxylic acid monohydrate Structure

3,5-Pyrazoledic...

~%

1-METHYL-1H-PYRAZOLE-3,5-DICARBOXYLIC ACID 3-METHYL ESTER Structure

1-METHYL-1H-PYR...

1H-Pyrazole-3,5-dicarbonyldichloride(9CI) Structure

1H-Pyrazole-3,5...

~%

1-METHYL-1H-PYRAZOLE-3,5-DICARBOXYLIC ACID 3-METHYL ESTER Structure

1-METHYL-1H-PYR...

5-((benzyloxycarbonyl)amino)-1-methylpyrazole-3-carboxylic acid Structure

5-((benzyloxyca...

~99%

1H-Pyrazole-3-carboxylicacid,5-amino-1-methyl-(9ci) Structure

1H-Pyrazole-3-c...

methyl 5-[(benzyloxycarbonyl)amino]-1-methylpyrazole-3-carboxylate Structure

methyl 5-[(benz...

~%

1H-Pyrazole-3-carboxylicacid,5-amino-1-methyl-(9ci) Structure

1H-Pyrazole-3-c...