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[ CAS No. 796729-03-8 ] {[proInfo.proName]}

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Chemical Structure| 796729-03-8
Chemical Structure| 796729-03-8
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Product Details of [ 796729-03-8 ]

CAS No. :796729-03-8 MDL No. :MFCD11846936
Formula : C7H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CSOYACNIOQHFQZ-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :11367096
Synonyms :

Calculated chemistry of [ 796729-03-8 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.43
Num. rotatable bonds : 1
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 38.11
TPSA : 55.12 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.91 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.84
Log Po/w (XLOGP3) : 0.45
Log Po/w (WLOGP) : 0.53
Log Po/w (MLOGP) : 0.33
Log Po/w (SILICOS-IT) : 0.45
Consensus Log Po/w : 0.52

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.34
Solubility : 7.0 mg/ml ; 0.046 mol/l
Class : Very soluble
Log S (Ali) : -1.18
Solubility : 10.2 mg/ml ; 0.0667 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.6
Solubility : 38.6 mg/ml ; 0.254 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.06

Safety of [ 796729-03-8 ]

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 [ 796729-03-8 ]

* 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 [ 796729-03-8 ]
  • Downstream synthetic route of [ 796729-03-8 ]

[ 796729-03-8 ] Synthesis Path-Upstream   1~3

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  • [ 86477-09-0 ]
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YieldReaction ConditionsOperation in experiment
57% With water; sodium hydroxide In 1,4-dioxane at 65℃; for 2.5 h; Example 162a
5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic Acid 162a
A 25-mL round-bottomed flask equipped with a reflux condenser was charged with ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate (540 mg, 3.0 mmol), 2N Aqueous sodium hydroxide solution (3.5 mL), and 1,4-dioxane (3.0 mL).
The system was heated at 65° C. for 2.5 h.
It was then cooled to room temperature and adjusted the pH to 2-3 with concentrated HCl.
The solid was collected by filtration to afford 162a (260 mg, 57percent) as a yellow solid. MS-ESI: [M+H]+ 153.3
Reference: [1] Patent: US2013/116246, 2013, A1, . Location in patent: Paragraph 0581
[2] Patent: EP1241170, 2002, A2, . Location in patent: Page 59
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  • [ 86477-10-3 ]
  • [ 86477-09-0 ]
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YieldReaction ConditionsOperation in experiment
81%
Stage #1: With potassium hydroxide In ethanol at 10 - 26℃; for 4.2 - 5.5 h;
Stage #2: With hydrogenchloride In water
A freshly prepared solution of potassium hydroxide (87.6percent w/w pellets, 307.6 g, 4.80 mol) in 2B ethanol (absolute, 1862 mL) is added over a period of 1 hour to a stirred solution of 1063.6 g [46.5percent strength (HPLC), 2.744 mol real)] of the ester mixture [(from example 5), ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate) and ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate] in 2B ethanol (absolute, 1276 mL) under a nitrogen atmosphere, while maintaining the temperature in the range 15-22° C. The mixture is stirred for 4-7 hours until ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate, is consumed, as determined by HPLC [Column: Zorbax Eclipse XDB-C8, 4.6.x.150 mm. Eluant: Acetonitrile/water; wavelength 225 nm. Retention times: potassium 5,6-dihydro-4H-pyrrolo-[1,2-b]pyrazole-2-carboxylate, 1.3 min., ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate, 6.4 min., ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate, 7.3 min., N-methoxy-N-methyl-5,6-dihydro-4H-pyrrolo[1,2-b]-pyrazole-2-carboxamide, 2.7 min.] The slurry is filtered and the filter cake is washed with 2B ethanol (1800-2400 ml in portions). The wet cake is dried under vacuum at 60-65° C. to constant weight. Crude potassium 5,6-dihydro-4H-pyrrolo-[1,2-b]pyrazole-2-carboxylate [426.3 g, 81percent (based on calcd. quantity of] is obtained as a tan, hygroscopic, solid, which is characterized using NMR, HPLC, KF and ash determinations. The cake may optionally be reslurried in 2B ethanol, if necessary, to remove impurities (such as potassium 5,6-dihydro-4H-pyrrolo-[1,2-b]pyrazole-3-carboxylic acid). The product of the example is used directly in the next step (see example 10). [TABLE-US-00002] Starting KOH/EtOH KOH/EtOH Reaction 2-Acid 2-Acid Crude esters Real Addition Addition Hold K Salt K Salt 2-Ester/3-Ester 2-Ester Time Temp Time Product percent yield (g) (g) (hours) ° C. (hours) (g) real to crude 587 275 1 20-25 4 249 85 1064 494 1 17-26 4 426 81 1967 948 1.5 16-18 4 816 81(a) 2700 1150 1.2 10-20 3 1039 86(a) (a)Reslurried with 4 volumes ethyl alcohol to remove residual impurities
48%
Stage #1: With sodium ethanolate In ethanol at 15 - 22℃; for 10 h;
Stage #2: With hydrogenchloride In water
Sodium ethoxide solution, in denaturated ethanol (21 wt percent, 12 ml, 38 mmol) is added to 6.9 g (38 mmol) of the crude mixture of esters, ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate and ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate in 3A ethanol (containing 3, 7percent water, 15 ml) and the mixture is stirred for 10 hours under a nitrogen atmosphere at 15-22° C. Consumption of ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate, is monitored by HPLC [Prodigy ODS3 4.6.x.150 mm column, 10 minutes gradient from 90:10 to 10:90 water/acetonitrile with 0.02percent trifluoroacetic acid, UV detection at 215 nm. Retention times under these conditions were: 2.6-2.7 min. for ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate (the desired, more polar isomer), 2.8-2.9 minutes for ethyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate (the undesired, less polar isomer) and 0.86 minutes for 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid]. The resulting mixture is evaporated under diminished pressure to a residue as a syrup. The syrup is mixed with ether (25 ml), and the resulting precipitate is collected on a filter. The hygroscopic filter cake is washed with diethyl ether (100 ml) and then dissolved in water (10 ml). The pH of the solution is adjusted to a value of 2 with 1N hydrochloric acid and the mixture extracted with ethyl acetate (3.x.25 ml). The combined organic extract is dried over magnesium sulfate and evaporated to give 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid as an off-white solid (1.40 g, 48percent), m.p. 140-145° C., which is characterized by NMR, mass spectrum, elemental analysis, and HPLC (Prodigy ODS3 4.6.x.150 mm column, with a 20 min gradient from 95:5 to 30:70 using water/acetonitrile with 0.02percent trifluoroacetic acid and UV detection at 215 nm. The retention time for 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylic acid was 7.2 minutes) The product of the example is used directly in the next step (see example 13).
Reference: [1] Patent: US2004/242874, 2004, A1, . Location in patent: Page 14-15
[2] Patent: US2004/242874, 2004, A1, . Location in patent: Page 14
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  • [ 98262-66-9 ]
  • [ 623-47-2 ]
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Reference: [1] Organic Process Research and Development, 2006, vol. 10, # 4, p. 712 - 716
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