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139756-22-2

Basic Information
CAS No.: 139756-22-2
Name: 5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
Article Data: 22
Molecular Structure:
Molecular Structure of 139756-22-2 (5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one)
Formula: C17H19ClN4O4S
Molecular Weight: 410.881
Synonyms: 4-ethoxy-3-(1-methyl-7-oxo-3-propyl-4H-pyrazolo[4,3-d]pyrimidin-5-yl)benzenesulfonyl chloride
Density: 1.48g/cm3
Melting Point: 180-182°C
Boiling Point: 621.4ºC at 760 mmHg
Flash Point: 329.6ºC
Appearance: Off-White to Pale Beige Solid
PSA: 115.32000
LogP: 3.68310
Synthetic route
139756-21-1

5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
With chlorosulfonic acid at 0 - 25℃; for 2h;97%
With chlorosulfonic acid In neat (no solvent) at 0 - 20℃; for 12h;95%
With chlorosulfonic acid; thionyl chloride at 0 - 20℃; Sealed tube;92%
36983-31-0

ethyl 3-butyrylpyruvate

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 10 steps
1: hydrazine hydrate / acetic acid; 2-methoxy-ethanol / 100 °C
2: caesium carbonate / N,N-dimethyl-formamide / 20 °C
3: hydrogenchloride / water / 100 °C
4: nitric acid; sulfuric acid / 50 °C
5: thionyl chloride / Reflux
6: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
7: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
8: triethylamine / dichloromethane / 20 °C
9: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
10: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 10 steps
1: acetic acid; hydrazine hydrate / 2-methoxy-ethanol / 100 °C
2: caesium carbonate / N,N-dimethyl-formamide / 20 °C
3: hydrogenchloride; water / 100 °C
4: sulfuric acid; nitric acid / 50 °C
5: thionyl chloride / Reflux
6: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
7: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
8: triethylamine / dichloromethane / 20 °C
9: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
10: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
107-87-9

2-Pentanone

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 11 steps
1.1: sodium / ethanol / 1 h / 20 °C
1.2: 20 °C
2.1: hydrazine hydrate / acetic acid; 2-methoxy-ethanol / 100 °C
3.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
4.1: hydrogenchloride / water / 100 °C
5.1: nitric acid; sulfuric acid / 50 °C
6.1: thionyl chloride / Reflux
7.1: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
8.1: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
9.1: triethylamine / dichloromethane / 20 °C
10.1: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
11.1: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 11 steps
1.1: sodium / ethanol / 1 h / 20 °C
1.2: 20 °C
2.1: acetic acid; hydrazine hydrate / 2-methoxy-ethanol / 100 °C
3.1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
4.1: hydrogenchloride; water / 100 °C
5.1: sulfuric acid; nitric acid / 50 °C
6.1: thionyl chloride / Reflux
7.1: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
8.1: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
9.1: triethylamine / dichloromethane / 20 °C
10.1: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
11.1: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
92945-27-2

ethyl 3-propyl-1H-pyrazole-5-carboxylate

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 9 steps
1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
2: hydrogenchloride / water / 100 °C
3: nitric acid; sulfuric acid / 50 °C
4: thionyl chloride / Reflux
5: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
6: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
7: triethylamine / dichloromethane / 20 °C
8: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
9: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 7 steps
1.1: 9 h / 5 - 25 °C
2.1: sodium hydroxide / 3 h / 75 °C
3.1: sulfuric acid; nitric acid / 8 h / 50 °C
4.1: thionyl chloride / 5 h / Reflux
5.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
6.1: ethanol / 1.5 h / 70 °C
6.2: 1.5 h / 70 °C
7.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 9 steps
1: caesium carbonate / N,N-dimethyl-formamide / 20 °C
2: hydrogenchloride; water / 100 °C
3: sulfuric acid; nitric acid / 50 °C
4: thionyl chloride / Reflux
5: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
6: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
7: triethylamine / dichloromethane / 20 °C
8: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
9: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
133261-07-1

1-Methyl-3-n-propylpyrazole-5-carboxylic acid ethyl ester

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 8 steps
1: hydrogenchloride / water / 100 °C
2: nitric acid; sulfuric acid / 50 °C
3: thionyl chloride / Reflux
4: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
5: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
6: triethylamine / dichloromethane / 20 °C
7: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
8: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 6 steps
1.1: sodium hydroxide / 3 h / 75 °C
2.1: sulfuric acid; nitric acid / 8 h / 50 °C
3.1: thionyl chloride / 5 h / Reflux
4.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
5.1: ethanol / 1.5 h / 70 °C
5.2: 1.5 h / 70 °C
6.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 8 steps
1: hydrogenchloride; water / 100 °C
2: sulfuric acid; nitric acid / 50 °C
3: thionyl chloride / Reflux
4: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
5: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
6: triethylamine / dichloromethane / 20 °C
7: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
8: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
139755-99-0

1-methyl-3-propyl-1 H-pyrazole-5-carboxylic acid

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 7 steps
1: nitric acid; sulfuric acid / 50 °C
2: thionyl chloride / Reflux
3: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
4: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
5: triethylamine / dichloromethane / 20 °C
6: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
7: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 5 steps
1.1: sulfuric acid; nitric acid / 8 h / 50 °C
2.1: thionyl chloride / 5 h / Reflux
3.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
4.1: ethanol / 1.5 h / 70 °C
4.2: 1.5 h / 70 °C
5.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 7 steps
1: sulfuric acid; nitric acid / 50 °C
2: thionyl chloride / Reflux
3: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
4: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
5: triethylamine / dichloromethane / 20 °C
6: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
7: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
139756-00-6

1-methyl-2-nitro-3-propyl-1H-pyrazole-5-carboxylic acid

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 6 steps
1: thionyl chloride / Reflux
2: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
3: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
4: triethylamine / dichloromethane / 20 °C
5: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
6: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 4 steps
1.1: thionyl chloride / 5 h / Reflux
2.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
3.1: ethanol / 1.5 h / 70 °C
3.2: 1.5 h / 70 °C
4.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 6 steps
1: thionyl chloride / Reflux
2: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
3: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
4: triethylamine / dichloromethane / 20 °C
5: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
6: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
139756-01-7

1-methyl-4-nitro-3-propyl-1H-pyrazole-5 carboxamide

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 4 steps
1: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
2: triethylamine / dichloromethane / 20 °C
3: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
4: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 3 steps
1.1: iron; ammonium chloride / ethanol; water / 4.5 h / 80 °C
2.1: ethanol / 1.5 h / 70 °C
2.2: 1.5 h / 70 °C
3.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 4 steps
1: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
2: triethylamine / dichloromethane / 20 °C
3: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
4: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
360068-47-9

1-methyl-4-nitro-3-propyl-1H-pyrazole-5-carbonyl chloride

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 5 steps
1: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
2: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
3: triethylamine / dichloromethane / 20 °C
4: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
5: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 5 steps
1: ammonium hydroxide / tetrahydrofuran / 2 h / Cooling with ice
2: palladium on activated charcoal; hydrogen / methanol / 30 °C / 2585.81 Torr
3: triethylamine / dichloromethane / 20 °C
4: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
5: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
139756-02-8

4-amino-1-methyl-3-propyl-1H-pyrazole-5-carboxamide

139756-22-2

5-(5-Chlorosulphonyl-2-ethoxyphenyl)-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one

Conditions
ConditionsYield
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 20 °C
2: sodium hydroxide; dihydrogen peroxide / ethanol; water / 100 °C
3: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
Multi-step reaction with 2 steps
1.1: ethanol / 1.5 h / 70 °C
1.2: 1.5 h / 70 °C
2.1: chlorosulfonic acid / 0 - 5 °C
View Scheme
Multi-step reaction with 3 steps
1: triethylamine / dichloromethane / 20 °C
2: sodium hydroxide; dihydrogen peroxide / water; ethanol / 100 °C
3: chlorosulfonic acid / 2 h / 20 °C / Cooling with ice
View Scheme
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