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[ CAS No. 268203-93-6 ]

{[proInfo.proName]} (Synonyms:Udenafil) ,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 268203-93-6
Chemical Structure| 268203-93-6
Structure of 268203-93-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 268203-93-6 ]

CAS No. :268203-93-6 MDL No. :MFCD20275557
Formula : C25H36N6O4S Boiling Point : -
Linear Structure Formula :- InChI Key :IYFNEFQTYQPVOC-UHFFFAOYSA-N
M.W :516.66 Pubchem ID :135413547
Synonyms :
Udenafil

Calculated chemistry of [ 268203-93-6 ]

Physicochemical Properties

Num. heavy atoms : 36
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.56
Num. rotatable bonds : 11
Num. H-bond acceptors : 8.0
Num. H-bond donors : 2.0
Molar Refractivity : 144.97
TPSA : 130.59 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -7.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.43
Log Po/w (XLOGP3) : 2.96
Log Po/w (WLOGP) : 3.53
Log Po/w (MLOGP) : 1.84
Log Po/w (SILICOS-IT) : 3.38
Consensus Log Po/w : 3.03

Druglikeness

Lipinski : 1.0
Ghose : None
Veber : 1.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -4.49
Solubility : 0.0167 mg/ml ; 0.0000323 mol/l
Class : Moderately soluble
Log S (Ali) : -5.37
Solubility : 0.00223 mg/ml ; 0.00000431 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.48
Solubility : 0.0000172 mg/ml ; 0.0000000333 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 4.76

Safety of [ 268203-93-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 268203-93-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 268203-93-6 ]

[ 268203-93-6 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 382592-28-1 ]
  • [ 268203-93-6 ]
YieldReaction ConditionsOperation in experiment
53% With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol for 8h; Heating / reflux; 2.11 Step 11 3-(1-Methyl-7-oxo-3-propyl-6,7-dihydro-1H-pyrazolo[4,3-d]pyrimidin-5-yl)-N-[2-(1-methyl-pyrrolidin-2-yl)-ethyl]-4-propoxy-benzenesulfonamide: Potassium tert-butoxide (0.9 g, 8.0 mmol) was added to a solution of crude 2-methyl-4-{5-[2-(1-methyl-pyrrolidin-2-yl)-ethylsulfamoyl]-2-propoxy-benzoylamino}-5-propyl-2H-pyrazole-3-carboxamide (2.14 g, 4.0 mmol) in dry tert-butanol (50 mL), and the mixture was heated to reflux for 8 hours. The reaction mixture was cooled to ambient temperature and diluted with ethyl acetate (300 mL). Following standard extractive work up, the solvent was evaporated under reduced pressure to yield a crude residue which was purified by flash chromatography to give the title compound (1.1 g, 53%). 1H NMR (300 MHz, CDCl3) δ 10.90 (broad s, 1H), 8.93 (s, 1H), 7.96 (d, 1H, J=8.7 Hz), 7.15 (d, 1H, J=8.7 Hz), 4.28-4.24 (m, 3H), 4.24 (s, 2H), 3.13 (t, 3H, J=6.9 Hz), 2.93 (t, 3H, J=7.8 Hz), 2.56 (s, 1H), 2.40 (s, 3H), 2.26-2.24 (m, 1H), 2.10-1.99 (m, 2H), 1.89-1.80 (m, 4H), 1.67 (s, 3H, J=7.2 Hz), 1.56-1.52 (m, 1H), 1.22 (t, 3H, J=7.5 Hz), 1.03 (t, 3H, J=7.2 Hz); LC-MS: m/z=517 (MH)+
With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol Reflux; 3 In step 3, 5-[2-propyloxy-5-(l-methyl-2-pyrrolidinylethyl amido- sulfonyl)phenyl]-l-methyl-3-propyl-l,6-dihydro-7H-pyrazolo(4,3-d)pyrimidin-7-one, a pyrazolopyrimidinone compound of the present invention, is prepared from the compound obtained in step 2. For preparation, a predetermined amount of the pyrazole compound synthesized in step 2 is dissolved in t-butanol, to which a predetermined amount of potassium t-butoxide is added, followed by stirring under reflux for a predetermined time. Upon completion of the reaction, the reaction solution is cooled down, diluted, washed and dried. Then, reduced pressure distillation, elimination of a solvent and silica gel column chromatography are performed to obtain a predetermined amount of a novel pyrazolopyrimidinone compound of the invention, represented by Chemical Formula 1.
With potassium <i>tert</i>-butylate In <i>tert</i>-butyl alcohol Heating / reflux; 3 In step 3, 5-[2-propyloxy-5-(l-methyl-2-pyrrolidinylethyl amidosulfonyl)phenyl] - l-methyl-3-propyl-l,6-dihydro-7H-pyrazolo(4,3-d)pyrimidin-7-one, which is pyrazolopyrimidine derivative of the present invention, is prepared from the compound obtained in step 2. Precisely, the proper amount of pyrazole compound synthesized in step 2 is dissolved in t-butanol, to which the proper amount of potassium t-butoxide is added, followed by reflux for a required time. Upon completion of reaction, the reaction solution is cooled down, diluted, washed and dried. Then, reduced pressure distillation, elimination of a solvent and silica gel column chromatographyare performed to give the novel pyrazolopyrimidine derivative of the invention.
  • 2
  • [ 268203-93-6 ]
  • [ 144-62-7 ]
  • udenafil oxalate [ No CAS ]
YieldReaction ConditionsOperation in experiment
89.5% In ethanol at 20℃; 1 ; Preparation of an oxalic acid addition salt of Udenafil; Ig of Udenafil was suspended in 10 mL of ethanol and agitated at room temperature. 0.25 g (1 equivalent) of oxalic acid was added dropwise into the reaction solution. After agitating the reaction solution for 1 hour at room temperature, the produced solid was filtered, washed with n-hexane 5 ml, and dried in vacuum. Consequently, white crystal of the title compound 1.05 g was obtained with a yield of 89.5%.lH-NMR(DMSO-d6) : 0.94 (m, 6H), 1.59 (m, 2H), 1.62 (m, 4H), 1.85 (m, 2H),1.96 (m, IH), 2.13 (m, IH), 2.69 (s, 3H), 2.85 (m, 2H), 2.95 (m, IH), 3.15 (m, IH), 4.08 (t, 2H), 4.15 (s, 3H), 7.33 (d, IH), 7.76(bs, IH), 7.87 (d, IH), 7.93 (s, IH), 12.16 (s, IH)
  • 3
  • [ 268203-93-6 ]
  • [ 124-04-9 ]
  • udenafil adipate [ No CAS ]
YieldReaction ConditionsOperation in experiment
90.6% In acetone at 20℃; 5 ; Preparation of an adipic acid addition salt of Udenafil; Ig of Udenafil was suspended in 10 mL of acetone and agitated at room temperature. 0.28 g (1 equivalent) of adipic acid was added dropwise into the reaction solution. After agitating the reaction solution for 3 hour at room temperature, the produced solid was filtered, washed with acetone 5 ml, and dried in vacuum. Consequently, white crystal of the title compound 1.16 g was obtained with a yield of 90.6%.IH-NMR (DMSO-d6) : 0.97 (m, 6H), 1.27 (m, 2H), 1.52 (m, 6H), 1.78 (m, 6H), 1.99 (m, 3H), 2.11 (s, 3H), 2.18 (m, 3H), 2.75 (m, 4H), 2.80 (m, IH), 4.06 (t, 2H), 4.15 (s, 3H), 7.32 (d, IH), 7.86 (d, IH), 7.93 (s, IH), 12.09(bs, IH)
  • 4
  • [ 268203-93-6 ]
  • [ 100-88-9 ]
  • [ 1240622-32-5 ]
YieldReaction ConditionsOperation in experiment
83.7% In ethyl acetate at 20℃; 6 ; Preparation of a cyclamic acid addition salt of Udenafil; Ig of Udenafil was suspended in 10 mL of ethylacetate and agitated at room temperature. 0.35 g (1 equivalent) of cyclamic acid was added dropwise into the reaction solution. After agitating the reaction solution for 3 hour at room temperature, the produced solid was filtered, washed with ethylacetate 5 ml, and dried in vacuum. Consequently, white crystal of the title compound 1.13 g was obtained with a yield of 83.7%.IH-NMR (DMSO-d6) : 0.93 (m, 6H), 1.03 (m, 3H), 1.16 (m, 2H), 1.36 (m, 5H), 1.77 (m, 4H), 1.89 (m, 5H), 2.13 (m, IH), 2.70 (m, 3H), 2.78 (t, 3H), 2.84 (m, 3H), 3.13 (m, IH), 3.46 (m, IH), 4.07 (t, 2H), 4.14 (s, 3H), 7.34 (d, IH), 7.73 (s, IH), 7.87 (d, IH), 7.94 (s, IH), 12.13 (s, IH)
  • 5
  • [ 268203-93-6 ]
  • [ 621-82-9 ]
  • udenafil cinnamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
79.1% In tetrahydrofuran at 20℃; 4 ; Preparation of a cinnamic acid addition salt of Udenafil; Ig of Udenafil was suspended in 10 mL of tetrahydrofuran and agitated at room temperature. 0.29 g (1 equivalent) of cinnamic acid was added dropwise into the reaction solution. After agitating the reaction solution for 3 hour at room temperature, the produced solid was filtered, washed with acetone 5 ml, and dried in vacuum.Consequently, white crystal of the title compound 1.02 g was obtained with a yield of79.1%.lH-NMR(DMSO-d6) : 0.92 (m, 6H), 1.27 (m, 2H), 1.54 (m, 2H), 1.67 (m, 5H),1.99 (m, 2H), 2.12 (s, 3H), 2.75 (m, 3H), 2.86 (m, IH), 3.59 (t, 2H), 4.08 (t, 2H), 4.15 (s,3H), 6.52 (d, IH), 7.33 (d, IH), 7.40 (m, 3H), 7.55 (d, IH), 7.66 (m, 2H), 7.85 (d, IH),7.94 (s, IH), 12.16(bs, IH)
  • 6
  • [ 268203-93-6 ]
  • [ 98-11-3 ]
  • [ 1240622-28-9 ]
YieldReaction ConditionsOperation in experiment
74.8% In methanol; acetonitrile at 20 - 80℃; 2 ; Preparation of a benzenesulfonic acid addition salt of Udenafil; Ig of Udenafil was suspended in 10 mL of acetonitrile and 1 mL of methanol and agitated at room temperature. 0.31 g (1 equivalent) of benzenesulfonic acid was added dropwise into the reaction solution. After agitating the reaction solution for 1 hour at 80 °C and then 1 hour at 50 °C, the produced solid was filtered, washed with acetone 5 mL, and dried in vacuum. Consequently, white crystal of the title compound 0.98 g was obtained with a yield of 74.8%.lH-NMR(DMSO-d) : 0.93 (m, 6H), 1.60 (m, 2H), 1.70 (m, 4H), 1.84 (m, IH),1.97 (m, 2H), 2.18 (m, IH), 2.81 (m, 7H), 3.05 (m, IH), 3.25 (m, IH), 3.53 (m, IH), 4.09 (t, 2H), 4.15 (s, 3H), 7.32 (m, 2H), 7.57 (d, IH), 7.76 (t, IH), 7.87 (d, IH), 7.94 (s,IH), 9.30(bs, IH), 12.15 (s, IH)
  • 8
  • [ 51387-90-7 ]
  • [ 139756-24-4 ]
  • [ 268203-93-6 ]
YieldReaction ConditionsOperation in experiment
85% at 10 - 20℃; for 1h; The reaction solution obtained in the previous step is cooled to below 10C. The starting material B', i.e. N-methyl-2-(2-aminoethyl)-pyrrolidine, was added dropwise (calculated as molar ratio Starting material B': Intermediate 1 = 3:1. After the addition was complete, the reaction was warmed to 20C for 1 h. The reaction was quenched by adding 260 mL of water and extracted once with 130 mL of dichloromethane. The organic phases are combined and washed once with 130 mL of 10% aqueous sodium bicarbonate. After washing once with 130 mL of saturated aqueous sodium chloride, The mixture was concentrated to dryness under reduced pressure at 45 C to give a white solid. Recrystallized from 260 mL of ethyl acetate and dried in vacuo at 45 C. to give 35. 1 g of white excellent enamidone (purity 99.72%, yield 85%).
  • 9
  • [ 139756-04-0 ]
  • [ 268203-93-6 ]
  • 10
  • [ 139756-23-3 ]
  • [ 268203-93-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: thionyl chloride; chlorosulfonic acid / 20 - 25 °C 2: 1 h / 10 - 20 °C
  • 11
  • [ 374776-34-8 ]
  • [ 268203-93-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: dichloromethane / 0 °C 2: potassium <i>tert</i>-butylate / <i>tert</i>-butyl alcohol / Heating / reflux
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