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[ CAS No. 139756-21-1 ] {[proInfo.proName]}

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Chemical Structure| 139756-21-1
Chemical Structure| 139756-21-1
Structure of 139756-21-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 139756-21-1 ]

CAS No. :139756-21-1 MDL No. :
Formula : C17H20N4O2 Boiling Point : -
Linear Structure Formula :- InChI Key :MXQUEDUMKWBYHI-UHFFFAOYSA-N
M.W : 312.37 Pubchem ID :135401477
Synonyms :
Chemical Name :5-(2-Ethoxyphenyl)-1-methyl-3-propyl-1H-pyrazolo[4,3-d]pyrimidin-7(6H)-one

Calculated chemistry of [ 139756-21-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 23
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.35
Num. rotatable bonds : 5
Num. H-bond acceptors : 4.0
Num. H-bond donors : 1.0
Molar Refractivity : 90.73
TPSA : 72.8 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : Yes
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.87
Log Po/w (XLOGP3) : 2.52
Log Po/w (WLOGP) : 2.67
Log Po/w (MLOGP) : 2.27
Log Po/w (SILICOS-IT) : 3.64
Consensus Log Po/w : 2.79

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.52
Solubility : 0.095 mg/ml ; 0.000304 mol/l
Class : Soluble
Log S (Ali) : -3.7
Solubility : 0.063 mg/ml ; 0.000202 mol/l
Class : Soluble
Log S (SILICOS-IT) : -5.87
Solubility : 0.000426 mg/ml ; 0.00000136 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.01

Safety of [ 139756-21-1 ]

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

Application In Synthesis of [ 139756-21-1 ]

* 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.

  • Upstream synthesis route of [ 139756-21-1 ]
  • Downstream synthetic route of [ 139756-21-1 ]

[ 139756-21-1 ] Synthesis Path-Upstream   1~1

  • 1
  • [ 139756-21-1 ]
  • [ 139756-22-2 ]
YieldReaction ConditionsOperation in experiment
76% for 12 h; Cooling with ice Example 1
Preparation of 5-(2-ethoxy-5-chlorosulfonyl)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyr azolo[4,3-d]pyrimidine-7-one
Chlorosulfuric acid (50ml)was added into a 100ml three-neck flask with a stirrer,
5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidi ne-7-one (31.2g (0.1mol)) was added in batches under stirring in an ice bath.
The reaction was exothermic and was performed for 12 hrs.
The reaction solution was slowly poured into icy water (100g), a white solid was separated out, filtered, dried.
A white solid (30g)was obtained with a yield of 76percent.
76% for 12 h; Cooling with ice Chlorosulfuric acid (50 ml) was added into a 100 ml three-neck flask with a stirrer, 5-(2-ethoxy)-phenyl-1-methyl-3-n-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-one (31.2 g (0.1 mol)) was added in batches under stirring in an ice bath. The reaction was exothermic and was performed for 12 hrs. The reaction solution was slowly poured into icy water (100 g), a white solid was separated out, filtered, dried. A white solid (30 g) was obtained with a yield of 76percent.
75.9% at -10 - 25℃; for 3 h; 4. Preparation of 5-(2-ethoxyphenyl-5-chlorosulphonyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-ketone (ZTH-4): [0031] At a temperature of −10° C., adding 5-(2-ethoxyphenyl)-1-methyl-3-propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-ketone (50 g, 160 mmo) into 100 ml chlorosulfonic acid, keeping the reaction solution at temperature no greater than 25° C. during dropping; upon dropping completes, reacting under room temperature for 3 hours; pouring the reaction liquid into crushed ice, mechanically stirring, keeping the temperature no greater than 25° C.; and then stirring under room temperature for 1 hour, filtering and drying, 50 g white solid ZTH-4 is obtained, wherein the yield is 75.9percent.
75% at 0 - 5℃; Step 8: Synthesis of 4-ethoxy-3-(6, 7-dihydro-1-methyl-7-oxo-3-propyl-1H-pyrazolo [4, 3-d] pyrimidin-5-yl) benzene-1-sulfonyl chloride:- To the chlorosulphonic acid (10 eq) was added 5-(2-ethoxyphenyl)- 1 -methyl-3-propyl- 1 H-pyrazolo[4,3 -d]pyrimidin-7(6H)- one (1 eq) while maintaining the temperature 0 °C. Then reaction was allowed toproceed at 5 °C until TLC analysis indicated the absence of starting material. After the reaction was completed then cooled CHC13 and ice in ice bath was added to the reaction mixture. Organic layer was separated. Water layer was re-extracted with 2 x 100 ml cold CHC13 and the combined organic layer are washed with brine solution, concentrated under vacuum; Yield 75percent. ‘H NMR (400 MHz, CDC13) 6 10.78(s 1H),8.72 (d, J= 1.4Hz, 1H), 8.04 (dd, J = 7.5, 1.4 Hz, 1H), 7.33 (d, J 7.5 Hz, 1H), 4.38(q J =6.8Hz2H),4.27(s 3H), 2.92(t J= 7.6 Hz 2H), l.87(m 2H), 1.65(t J= 6.8Hz 3H). l.02(t J=7.2Hz 3H). ESI [M + H] : 411.13
50 g at -10 - 25℃; for 3 h; At a temperature of -10°C, adding 5-(2- ethoxyphenyl)-1- methyl-3- propyl-1,6-dihydro-7H-pyrazolo[4,3-d]pyrimidine-7-ketone (50g, 160mmo) into 100ml chlorosulfonic acid, keeping the reaction solution at temperature no greaterthan 25°C during dropping; upon dropping completes, reacting under room temperature for 3 hours; pouring the reactionliquid into crushed ice, mechanically stirring, keeping the temperature no greater than 25°C; and then stirring under roomtemperature for 1 hour, filtering and drying, 50g white solid ZTH-4 is obtained, wherein the yield is 75.9percent.
2.0 g at 20℃; for 2 h; Cooling with ice I-09a (2.5 g, 8.0 mmol) was added into CISO3H (R-05, 10 mL) at ice-water and stirred at r.t. for 2 hours. The reaction mixture was quenched by adding water, and then filtrated. The filtrate cake was collected and dried under vacuo to give I-i Oa (2.0 g) ESI-MS (Mi-i): 411 calc. for C17H19C1N404S: 410.1.
2 g at 20℃; for 2 h; Cooling with ice Preparation of intermediate 1-10a: 4-Ethoxy-3-(6,7-dihvdro-1 -methyl-7-oxo-3- propyl-1 H-pyrazolo[4,3-c lpyrimidin-5-yl)benzene-1 -sulfonyl chloride l-09a (2.5 g, 8.0 mmol) was added into CISO3H (R-05, 10 ml_) at ice-water and stirred at r.t. for 2 hours. The reaction mixture was quenched by adding water, and then filtrated. The filtrate cake was collected and dried under vacuo to give 1-10a (2.0 g) ESI-MS (M+1 ): 41 1 calc. for d7H19CIN4O4S: 410.1.

Reference: [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
[6] Patent: US2014/18351, 2014, A1, . Location in patent: Paragraph 0044; 0045
[7] Patent: US2013/116265, 2013, A1, . Location in patent: Paragraph 0030; 0031
[8] Patent: WO2015/114647, 2015, A1, . Location in patent: Page/Page column 48
[9] Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry, 2010, vol. 49, # 1, p. 84 - 88
[10] Journal of the Indian Chemical Society, 2008, vol. 85, # 10, p. 1045 - 1049
[11] Journal of Medicinal Chemistry, 2016, vol. 59, # 19, p. 8967 - 9004
[12] Patent: EP2589601, 2013, A1, . Location in patent: Paragraph 0019; 0030; 0031
[13] Patent: WO2014/131855, 2014, A1, . Location in patent: Page/Page column 82
[14] Patent: WO2016/20307, 2016, A1, . Location in patent: Page/Page column 51
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