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

Synthesis and properties of isoviagra. A 2??methyl??2H??pyrazolo [4, 3??d] pyrirnidin??7??one isomer of viagra®

MM El??Abadelah, SS Sabri, MA Khanfar…

Index: El-Abadelah, Mustafa M.; Sabri, Salim S.; Khanfar, Monther A.; Yasin, Hani A.; Voelter, Wolfgang Journal of Heterocyclic Chemistry, 2002 , vol. 39, # 5 p. 1055 - 1059

Full Text: HTML

Citation Number: 9

Abstract

Abstract The synthesis and spectral properties (ir, ms, nmr) of a substituted 2-methyl-2H- pyrazolo [4, 3-d]-pyrimidin-7-one (3), an isomer of Viagra®, are described. The key synthon, 4-amino-1-methyl-5-propyl-3-pyrazolecarboxamide (7), is prepared via the reaction of ethyl 2, 4-dioxoheptanoate with methylhydrazine, followed by cyclization, nitration, amidation, and nitro group reduction. Interaction of 7 with 2-ethoxyben-zoyl chloride yielded the ...

1-Methyl-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-5-prop...

~80%

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-4-nitr...

Ethyl 2,4-dioxoheptanoate Structure

Ethyl 2,4-dioxo...

monomethylhydrazine Structure

monomethylhydrazine

~31%

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-4-nitr...

2-Ethoxybenzoic acid Structure

2-Ethoxybenzoic acid

4-Amino-1-methyl-5-propyl-1H-pyrazole-3-carboxylic acid amide Structure

4-Amino-1-methy...

~88%

4-[(2-Ethoxybenzoyl)amino]-1-methyl-5-propyl-1H-pyrazole-3-carboxamide Structure

4-[(2-Ethoxyben...

Ethyl 2,4-dioxoheptanoate Structure

Ethyl 2,4-dioxo...

~%

4-[(2-Ethoxybenzoyl)amino]-1-methyl-5-propyl-1H-pyrazole-3-carboxamide Structure

4-[(2-Ethoxyben...

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide Structure

1-Methyl-4-nitr...

~%

4-[(2-Ethoxybenzoyl)amino]-1-methyl-5-propyl-1H-pyrazole-3-carboxamide Structure

4-[(2-Ethoxyben...

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-4-nitr...

~%

4-[(2-Ethoxybenzoyl)amino]-1-methyl-5-propyl-1H-pyrazole-3-carboxamide Structure

4-[(2-Ethoxyben...

1-Methyl-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-5-prop...

~%

4-[(2-Ethoxybenzoyl)amino]-1-methyl-5-propyl-1H-pyrazole-3-carboxamide Structure

4-[(2-Ethoxyben...

Ethyl 2,4-dioxoheptanoate Structure

Ethyl 2,4-dioxo...

~%

5-(2-Ethoxyphenyl)-2,6-dihydro-2-Methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-(2-Ethoxyphen...

2-Ethoxybenzoic acid Structure

2-Ethoxybenzoic acid

4-Amino-1-methyl-5-propyl-1H-pyrazole-3-carboxylic acid amide Structure

4-Amino-1-methy...

~29%

5-(2-Ethoxyphenyl)-2,6-dihydro-2-Methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-(2-Ethoxyphen...

4-[(2-Ethoxybenzoyl)amino]-1-methyl-5-propyl-1H-pyrazole-3-carboxamide Structure

4-[(2-Ethoxyben...

~33%

5-(2-Ethoxyphenyl)-2,6-dihydro-2-Methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-(2-Ethoxyphen...

1-Methyl-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-5-prop...

~%

5-(2-Ethoxyphenyl)-2,6-dihydro-2-Methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-(2-Ethoxyphen...

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide Structure

1-Methyl-4-nitr...

~%

5-(2-Ethoxyphenyl)-2,6-dihydro-2-Methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-(2-Ethoxyphen...

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-4-nitr...

~%

5-(2-Ethoxyphenyl)-2,6-dihydro-2-Methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-(2-Ethoxyphen...

2-Ethoxybenzoic acid Structure

2-Ethoxybenzoic acid

~%

5-(2-Ethoxyphenyl)-2,6-dihydro-2-Methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-(2-Ethoxyphen...

4-Amino-1-methyl-5-propyl-1H-pyrazole-3-carboxylic acid amide Structure

4-Amino-1-methy...

~%

5-(2-Ethoxyphenyl)-2,6-dihydro-2-Methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-(2-Ethoxyphen...

5-(2-Ethoxyphenyl)-2,6-dihydro-2-Methyl-3-propyl-7H-pyrazolo[4,3-d]pyrimidin-7-one Structure

5-(2-Ethoxyphen...

~89%

4-ethoxy-3-(2-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride Structure

4-ethoxy-3-(2-m...

Ethyl 2,4-dioxoheptanoate Structure

Ethyl 2,4-dioxo...

~%

4-ethoxy-3-(2-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride Structure

4-ethoxy-3-(2-m...

2-Ethoxybenzoic acid Structure

2-Ethoxybenzoic acid

~%

4-ethoxy-3-(2-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride Structure

4-ethoxy-3-(2-m...

4-Amino-1-methyl-5-propyl-1H-pyrazole-3-carboxylic acid amide Structure

4-Amino-1-methy...

~%

4-ethoxy-3-(2-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride Structure

4-ethoxy-3-(2-m...

1-Methyl-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-5-prop...

~%

4-ethoxy-3-(2-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride Structure

4-ethoxy-3-(2-m...

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide Structure

1-Methyl-4-nitr...

~%

4-ethoxy-3-(2-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride Structure

4-ethoxy-3-(2-m...

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-4-nitr...

~%

4-ethoxy-3-(2-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride Structure

4-ethoxy-3-(2-m...

4-[(2-Ethoxybenzoyl)amino]-1-methyl-5-propyl-1H-pyrazole-3-carboxamide Structure

4-[(2-Ethoxyben...

~%

4-ethoxy-3-(2-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride Structure

4-ethoxy-3-(2-m...

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxylic Acid Structure

1-Methyl-4-nitr...

~86%

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide Structure

1-Methyl-4-nitr...

1-Methyl-4-nitro-5-propyl-1H-pyrazole-3-carboxamide Structure

1-Methyl-4-nitr...

~89%

4-Amino-1-methyl-5-propyl-1H-pyrazole-3-carboxylic acid amide Structure

4-Amino-1-methy...

Synthesis and properties of isoviagra. A 2??methyl??2H??pyra...

[Journal of Heterocyclic Chemistry, , vol. 39, # 5 p. 1055 - 1059]