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[ CAS No. 796729-10-7 ] {[proInfo.proName]}

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Chemical Structure| 796729-10-7
Chemical Structure| 796729-10-7
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Product Details of [ 796729-10-7 ]

CAS No. :796729-10-7 MDL No. :MFCD11846937
Formula : C7H8N2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :CCRGDNIETIHGAG-UHFFFAOYSA-N
M.W : 152.15 Pubchem ID :69319994
Synonyms :

Calculated chemistry of [ 796729-10-7 ]

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) : -7.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.91
Log Po/w (XLOGP3) : 0.12
Log Po/w (WLOGP) : 0.53
Log Po/w (MLOGP) : 0.33
Log Po/w (SILICOS-IT) : 0.45
Consensus Log Po/w : 0.47

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.13
Solubility : 11.3 mg/ml ; 0.0743 mol/l
Class : Very soluble
Log S (Ali) : -0.83
Solubility : 22.3 mg/ml ; 0.147 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 : 1.9

Safety of [ 796729-10-7 ]

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 [ 796729-10-7 ]

* 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 [ 796729-10-7 ]

[ 796729-10-7 ] Synthesis Path-Downstream   1~18

  • 2
  • [ 796729-10-7 ]
  • [ 100-51-6 ]
  • benzyl (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 1110℃; Add <strong>[796729-10-7]5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid</strong> (0.81 g, 5.3 mmol) and 15 mL of 1,4-dioxane, benzyl alcohol to a 50 mL single-mouth vial (0.83 mL, 8.0 mmol), DIPEA (1.8 mL, 11.0 mmol), and DPPA (2.20 g,8.0 mmol), refluxing at 110 C overnight, the reaction was completed by TLC, cooled to 0 C, suction filtration,Obtained 0.98 g of a pale yellow solid in a yield of 72%.
With diphenylphosphoranyl azide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 110℃; for 2.0h; To a solution of 5,6-dihydro-4H-pyrrolo[l ,2-b]pyrazole-3-carboxylic acid (24.2 mg, 0.159 mmol) in dioxane (2.0 mL) and benzyl alcohol (0.0333 mL, 0.318 mmol) was added N V- diisopropylethylamine (0.0834 mL, 0.477 mmol) and diphenylphosphoryl azide (0.0354 mL, 0.159 mmol). The mixture was then heated to 110 C for 2 hours. The reaction mixture was concentrated in vacuo and purified by reverse-phase HPLC to afford the title compound with an unidentified byproduct. This material was used directly in the next step.
  • 3
  • [ 86477-10-3 ]
  • [ 796729-10-7 ]
YieldReaction ConditionsOperation in experiment
87% With water; sodium hydroxide; In ethanol; at 0 - 20℃; Add 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid ethyl ester (2.20 g, 12 mmol) and 20 mL of ethanol and 5 mL of water to a 100 mL vial, and cool to 0 C.Add sodium hydroxide solid (2.7 g, 49 mmol), stir to dissolve, transfer to room temperature overnight, and complete the reaction by TLC to spin off the ethanol.Add 5 mL of dissolved solids in water and adjust the pH to 3-4 with 4N HCl in an ice bath.Precipitate solids, suction filtration,Obtained 1.62 g of a pale yellow solid with a yield of 87%.
62% To a vial containing ethyl 5,6-dihydro-4H-pyrrolo[l,2-b]pyrazole-3-carboxylate (171 mg, 0.95 mmol) was added water (5 mL) followed by potassium hydroxide (266.20 mg, 4.74 mmol). The vial was capped with a teflon-lined cap and heated to 80 C for 3 h. The product was acidified with concentrated HCl and concentrated in vacuo. The crude residue was taken up in EtOAc and filtered. The filtrate was concentrated in vacuo to afford the title compound as a white solid (89 mg, 62%). 1H NMR (400 MHz, CDC13) delta 7.18 (s, 1H), 4.05 (t, J= 7.2 Hz, 2H), 2.84 - 2.75 (m, 2H), 2.70 (s, 2H), 2.63 - 2.49 (m, 2H). FontWeight="Bold" FontSize="10" H NMR (400 MHz, DMSO) delta 12.06 (s, 1H), 7.75 (s, 1H), 4.12 - 4.06 (m, 2H), 3.00 - 2.92 (m, 2H), 2.61 - 2.52 (m, 2H). LC-MS (ESI): m/z = 153.0 (M+H)+.
  • 4
  • [ 796729-10-7 ]
  • 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-amine [ No CAS ]
  • 5
  • methyl 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-2-carboxylate [ No CAS ]
  • methyl 5, 6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate [ No CAS ]
  • [ 796729-03-8 ]
  • [ 796729-10-7 ]
YieldReaction ConditionsOperation in experiment
With water; sodium hydroxide; In methanol; at 50℃; for 5.0h; [0546j To a solution of methyl 5 ,6-dihydro-4H-pyrrolo [1 ,2-b]pyrazole-2-carboxylate and methyl 5 ,6-dihydro-4H-pyrrolo [1 ,2-b]pyrazole-3 -carboxylate (3.5 g, 21.0 mmol) in MeOH (50 mL) was added NaOH (2.5 g, 63.0 mmol) and stirred at 50 C for 5 h. Water (50 mL) was added, the mixture was adjusted to pH = 6 with concentrated HC1, extracted with EtOAc (100 mL x 2), dried and concentrated in vacuo to afford the crude product (2.2 g, yield: 69%) which was used in the next step without further purification. ?H NMR (400 MHz, CDC13) (5: 7.90 (s, 1H), 3.09 (t,J= 7.2 Hz, 2H), 2.47 (t,J= 7.2 Hz, 2H), 2.22-2.15 (m, 2H).
  • 6
  • [ 796729-03-8 ]
  • [ 64-17-5 ]
  • [ 796729-10-7 ]
  • ethyl (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)carbamate [ No CAS ]
  • ethyl (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-2-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
23%; 9% With diphenyl phosphoryl azide; N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 20 - 110℃; for 4.0h; [0547j To a solution of the above mixture (1.0 g, 6.6 mmol) in dioxane (20 mL) was added DIPEA (2.5 g, 19.8 mmol) and DPPA (1.8 g, 6.6 mmol) and stirred at rt for 2 h. EtOH (10 mL) was added and the mixture was heated to 110 C for 2 h. The solvent was removed in vacuo, the crude product was purified by silica gel column chromatography (petroleum ether: EtOAc = 1:3) to give a white solid. The solid was suspended in MeOH (15 mL), filtered, and the filtrate was concentrated in vacuo to give (5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)carbamate (300 mg, yield: 23%) as a white solid. The white precipitate is ethyl (5,6-dihydro-4H-pyrrolo[1,2- b]pyrazol-2-yl)carbamate (120 mg, yield: 9%). ESI-MS (M+H) : 196.1.
  • 7
  • methyl 5, 6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylate [ No CAS ]
  • [ 796729-10-7 ]
YieldReaction ConditionsOperation in experiment
With water; lithium hydroxide; In tetrahydrofuran; at 20℃; Step 2: Synthesis of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid (CF70) CF66-2 (315 mg) was dissolved in THF (5 mL). Water (5 mL) and LiOH-H2O (2 g) were added subsequently and the solution was stirred at ambient temperature for overnight. The aqueous was extracted with diethyl ether and subsequently acidified with 1 N HCl. The aqueous layer was extracted with ethyl acetate. The organic layers were combined, dried, and concentrated on a rotary evaporator. The remaining residue containing CF70 (280 mg) was used without further purification. 1H NMR (300 MHz, MeOD-d4): 7.83 (s, 1H), 4.14 (t, J=7.30 Hz, 2H), 3.07 (t, J=7.38 Hz, 2H), 2.74-2.60 (m, 4H). 13C NMR (75 MHz, MeOD-d4):164.99, 150.21, 144.61, 107.63, 47.51, 25.24, 23.08. ESI-MS calculated for C7H9N2O2 [M+H]+=153.07, Observed: 153.08.
  • 8
  • [ 796729-10-7 ]
  • N-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)-7-(3,5-dimethylisoxazol-4-yl)-6-methoxy-2-methyl-9H-pyrimido[4,5-b]indol-4-amine trifluoroacetate [ No CAS ]
  • 9
  • [ 796729-10-7 ]
  • [ 75-65-0 ]
  • tert-butyl(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)carbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
224 mg With diphenyl phosphoryl azide; triethylamine; for 24.0h;Reflux; Step 3: Synthesis of tert-butyl(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)carbamate (CF72) CF70 (280 mg, 1.84 mmol) was mixed with tert-butanol (6 mL) and triethyl amine (0.8 mL, 4 mmol). Diphenyl phosphoryl azide (0.71 mL, 3.31 mmol) was added via a syringe and the mixture was stirred at ambient temperature for overnight. The solution was heated at reflux for 24 h. The volatile components were removed on a rotary evaporator and the residue was purified by flash column chromatography. CF72 was isolated in 224 mg. 1H NMR (300 MHz, CDCl3): 7.36 (s, 1H), 6.24 (s, 1H), 4.05 (t, J=7.31 Hz, 2H), 2.98-2.82 (m, 2H), 2.60-2.44 (m, 4H), 1.46 (s, 9H). 13C NMR (75 MHz, CDCl3): 153.76, 137.82, 137.01, 114.08, 80.10, 48.23, 28.48, 26.26, 23.63. ESI-MS calculated for C11H18N3O2 [M+H]+=224.14, Observed: 224.58.
  • 10
  • [ 796729-10-7 ]
  • 3-iodo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole [ No CAS ]
YieldReaction ConditionsOperation in experiment
76% With N-iodo-succinimide; sodium hydrogencarbonate; In N,N-dimethyl-formamide; at 17 - 60℃; for 31.0h; 5,6-Dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid (0.75 g, 4.93 mmol) dissolved in DMF (4 mL) was treated with N-iodosuccinimide (1.331 g, 5.92 mmol) and sodium bicarbonate (0.497 g, 5.92 mmol) at r.t. The mixture was stirred at r.t. for 15 h. The reaction was stirred at 60 C. for a further 16 h and then concentrated under reduced pressure. The resulting residue was dissolved in EtOAc (50 mL) and washed with water (2×50 mL). The organic layer was concentrated under reduced pressure, and the crude product was purified by flash silica chromatography, elution gradient 0 to 70% EtOAc in heptane. Pure fractions were evaporated to dryness to afford 3-iodo-5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole (0.88 g, 76%) as a beige solid. 1H NMR (400 MHz, DMSO-d6, 30 C.) 2.53-2.6 (2H, m), 2.69-2.79 (2H, m), 4.04-4.19 (2H, m), 7.46 (1H, s). m/z: ES+[M+H]+ 235.
  • 11
  • [ 796729-10-7 ]
  • [ 1314138-13-0 ]
  • 12
  • [ 796729-10-7 ]
  • tert-butyl ((1R,3S)-3-((5-chloro-4-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)pyridin-2-yl)carbamoyl)cyclohexyl)carbamate [ No CAS ]
  • 13
  • [ 796729-10-7 ]
  • (1S,3R)-3-amino-N-(5-chloro-4-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)pyridin-2-yl)cyclohexanecarboxamide dihydrochloride [ No CAS ]
  • 14
  • [ 796729-10-7 ]
  • 5-((5-chloro-2-((5,6-dihydro-4H-pyrrole[1,2-b]pyrazol-3-yl)amino)pyridin-4-yl)amino)-2-methyl-3,4-dihydroisoquinoline-1(2H)-one [ No CAS ]
  • 15
  • [ 796729-10-7 ]
  • 5-((2-((5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)amino)-5-(trifluoromethyl)pyrimidine-4-yl)amino)-2-methyl-3,4-dihydroisoquinolin-1(2H)-one [ No CAS ]
  • 16
  • [ 796729-10-7 ]
  • butyl 2-((5-chloro-2-((5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)amino)pyridin-4-yl)amino)benzoate [ No CAS ]
  • 17
  • [ 796729-10-7 ]
  • 2-({5-chloro-2-[(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazol-3-yl)amino]pyridin-4-yl}amino)-N-methoxybenzamide [ No CAS ]
  • 18
  • [ 660838-05-1 ]
  • [ 796729-10-7 ]
  • tert-butyl 3-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxamido)-4-methylphenylcarbamate [ No CAS ]
YieldReaction ConditionsOperation in experiment
Stage #1: 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid With N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In N,N-dimethyl-formamide at 25℃; for 0.166667h; Stage #2: t-butyl 3-amino-4-methylphenylcarbamate With N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 25℃; for 1h; Tert-butyl 3-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxamido)-4- methylphenylcarbamate To a solution of 5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxylic acid (164.28 mg, 1.08 mmol, 1.2 eq) in DMF (3 mL) was added HATU (513.17 mg, 1.35 mmol, 1.5 eq) stirred at 25°C for 10 min. And then was added DIEA (348.86 mg, 2.70 mmol, 470.16 µL, 3 eq) and tert-butyl 3-amino-4-methylphenylcarbamate (200 mg, 899.75 µmol, 1 eq). The mixture was stirred at 25°C for 1h. LCMS showed the starting material was consumed and the desired MS (M+1,357.2) was detected. Reaction mixture was added to the H2O (30 mL) with stirred. And then was filtered and concentrated to give a white solid. The residue was used into the next step without purification. The crude product tert-butyl 3-(5,6-dihydro-4H-pyrrolo[1,2-b]pyrazole-3-carboxamido)-4- methylphenylcarbamate (300 mg, 841.71 µmol, 93.55% yield) as a white solid was obtained. 1H-NMR (400 MHz, METHANOL-d4) ppm = 7.79 - 7.70 (m, 1H), 7.27 - 7.09 (m, 2H), 6.59 - 6.51 (m, 1H), 4.24 - 4.16 (m, 2H), 3.00 - 2.95 (m, 2H), 2.72 - 2.60 (m, 2H), 2.26 - 2.23 (m, 3H), 1.53 - 1.50 (m, 9H). LCMS: Retention time: 0.993 min, [M+H]+ calcd. for C19H24N4O3357.2; found 357.4
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