| Identification | Back Directory | [Name]
5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one | [CAS]
139756-22-2 | [Synonyms]
Sildenafil Impurity 7
Sildenafil intermediate
Sildenafil Chlorosulfone IMpurity
Sildenafil Chlorosulfonyl IMpurity
5-(5-CHLOROSULFONYL-2-ETHOXY PHENYL)-1-METHYL-3-N-PROPYL-1
3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1 H-pyrazolo-(4-3-d)-pyrimidine-5
4-Ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)
4-Ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo-[4,3-d]pyrimidin-5-yl)benzene-1-su
4-Ethoxy-3-(1-methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo-[4,3-d]pyrimidin-5-yl)benzene-1-sulfo
5-(5-Chlorosulfonyl-2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one
3-(4,7-Dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-4-ethoxy-benzenesulfonyl Chloride
4-Ethoxy-3-(6,7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-5-yl)benzene-1-sulfonyl chloride
4-Ethoxy-3-(1-Methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyriMidin-5-yl)benzene-1-sulfonyl chloride | [Molecular Formula]
C17H19ClN4O4S | [MDL Number]
MFCD09753597 | [MOL File]
139756-22-2.mol | [Molecular Weight]
410.88 |
| Chemical Properties | Back Directory | [Appearance]
Off-White Solid | [Melting point ]
180-182°C | [density ]
1.48±0.1 g/cm3(Predicted) | [storage temp. ]
-20°C Freezer, Under Inert Atmosphere | [solubility ]
Chloroform (Slightly), Methanol (Slightly, Heated) | [form ]
Solid | [pka]
9.87±0.20(Predicted) | [color ]
White to Pale Beige | [Stability:]
Moisture Sensitive | [InChI]
InChI=1S/C17H19ClN4O4S/c1-4-6-12-14-15(22(3)21-12)17(23)20-16(19-14)11-9-10(27(18,24)25)7-8-13(11)26-5-2/h7-9H,4-6H2,1-3H3,(H,19,20,23) | [InChIKey]
RVVOSOSBFSYZDM-UHFFFAOYSA-N | [SMILES]
C1(S(Cl)(=O)=O)=CC=C(OCC)C(C2NC(=O)C3N(C)N=C(CCC)C=3N=2)=C1 | [CAS DataBase Reference]
139756-22-2 |
| Hazard Information | Back Directory | [Chemical Properties]
Off-White Solid | [Uses]
The compound Sildenafil Chlorosulfonyl Impurity (139756-22-2) is a derivative of Sildenafil. It is widely used in the treatment of pulmonary hypertension as it is capable of inhibiting cGMP and acts as a potent selective inhibitor of PDE5. | [Description]
Sildenafil chlorosulfonyl is a synthetic intermediate in the synthesis of the phosphodiesterase 5 (PDE5) inhibitor sildenafil. It is also a potential impurity found in commercial preparations of sildenafil. | [Synthesis]
Example 1 Preparation of 5-(2-ethoxy-5-chlorosulfonyl)phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one: Chlorosulfuric acid (50 mL) was added to a 100 mL three-neck flask and placed in an ice bath. Under stirring, 5-(2-ethoxy)phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidin-7-one (31.2 g, 0.1 mol) was added in batches. The reaction was exothermic and stirred continuously for 12 hours. Upon completion of the reaction, the reaction solution was slowly poured into ice water (100 g) and a white solid precipitated. The solid was collected by filtration and dried to give a white solid product (30 g) in 76% yield. | [storage]
-20°C | [References]
[1] Journal of Medicinal Chemistry, 2008, vol. 51, # 9, p. 2807 - 2815
[2] Angewandte Chemie - International Edition, 2017, vol. 56, # 1, p. 221 - 224
[3] Angew. Chem., 2017, vol. 129, # 1, p. 227 - 230,4
[4] Chemical Communications, 2016, vol. 52, # 67, p. 10245 - 10248
[5] Patent: EP2666776, 2013, A1. Location in patent: Paragraph 0022; 0023 |
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