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[ CAS No. 1350325-05-1 ] {[proInfo.proName]}

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Chemical Structure| 1350325-05-1
Chemical Structure| 1350325-05-1
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Product Details of [ 1350325-05-1 ]

CAS No. :1350325-05-1 MDL No. :MFCD27665102
Formula : C4H5IN2O Boiling Point : -
Linear Structure Formula :- InChI Key :AKAILQXICKUNET-UHFFFAOYSA-N
M.W : 224.00 Pubchem ID :67004784
Synonyms :

Calculated chemistry of [ 1350325-05-1 ]

Physicochemical Properties

Num. heavy atoms : 8
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.25
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 37.8
TPSA : 37.91 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.84 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : 1.17
Log Po/w (WLOGP) : 1.02
Log Po/w (MLOGP) : 0.79
Log Po/w (SILICOS-IT) : 2.01
Consensus Log Po/w : 1.26

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.36
Solubility : 0.972 mg/ml ; 0.00434 mol/l
Class : Soluble
Log S (Ali) : -1.56
Solubility : 6.15 mg/ml ; 0.0275 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.32
Solubility : 1.07 mg/ml ; 0.00479 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.45

Safety of [ 1350325-05-1 ]

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 [ 1350325-05-1 ]

* 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.

  • Downstream synthetic route of [ 1350325-05-1 ]

[ 1350325-05-1 ] Synthesis Path-Downstream   1~8

  • 1
  • [ 23511-05-9 ]
  • [ 1350325-05-1 ]
  • [ 1350325-04-0 ]
YieldReaction ConditionsOperation in experiment
With caesium carbonate; In N,N-dimethyl-formamide; at 100℃; for 19h; 1-(1,4-Dioxaspiro[4.5]dec-8-yl)-<strong>[1350325-05-1]4-iodo-3-methoxy-1H-pyrazole</strong> A solution of <strong>[1350325-05-1]4-iodo-3-methoxy-1H-pyrazole</strong> (0.783 g, 3.50 mmol), 1,4-dioxaspiro[4.5]dec-8-yl 4-methylbenzenesulfonate (1.20 g, 3.84 mmol), and Cs2CO3 (1.71 g, 5.24 mmol) in anhydrous degassed DMF (26.1 mL) was heated to 100 C. for 3 h. From LCMS, there was still starting material (pyrazole) therefore the reaction mixture was charged with an additional 1,4-dioxaspiro[4.5]dec-8-yl 4-methylbenzenesulfonate (0.437 g, 1.40 mmol) and Cs2CO3 (0.683 g, 2.10 mmol) and heated to 100 C. for an additional 16 h. The reaction mixture was partitioned between EtOAc (100 mL) and H2O (25 mL) and separated. The aqueous was re-extracted with EtOAc (3*) and the combined organic fractions were washed with H2O (3*25 mL), brine (1*), dried over Na2SO4, filtered and concentrated in vacuo resulting in 1.29 g of a crude orange oil/solid mixture. The crude was crystallized from MeOH and the white crystals were filtered through a fritted funnel resulting in the title compound as white crystals. 1H NMR (400 MHz, CD3OD): delta=1.63-1.74 (m, 2H), 1.81-1.89 (m, 2H), 1.98-2.07 (m, 4H), 3.87 (s, 3H), 3.91-3.99 (m, 4H), 4.00-4.09 (m, 1H), 7.48 (s, 1H). MS (ES+): m/z 365.05 [MH+]. HPLC: tR=3.98 min (polar-5 min, ZQ3).
  • 2
  • [ 215610-30-3 ]
  • [ 1350325-05-1 ]
YieldReaction ConditionsOperation in experiment
58% With N-iodo-succinimide; In N,N-dimethyl-formamide; at -30℃; for 1.5h; Compound 48F: 4-iodo-3(5)-methoxypyrazoleA solution of 3-methoxy-1 H-pyrazole (Compound 48G, 1.6 g, 16.32 mmol) in DMF (25 mL) was cooled to -30 C and charged with NIS (3.67 g, 16.31 mmol). The reaction mixture was stirred at -30 C for 1.5 h, and then H20 (30 mL) and EtOAc (40 mL) were added at -30 C. Organic layer was separated and the aqueous layer was re-extracted with EtOAc (3 x 20 mL) and the combined organic fractions were washed with H20, 1 M aqueous Na2S203, followed by brine, dried over Na2S04, filtered and concentrated in vacuo to afford 2.1 g (58 %) of the title compound as a light yellow solid. This material was taken on to the next step without further purification. 1H NMR (300 MHz, CDCI3) delta 7.41 (s, 1 H), 3.96 (s, 3H).
With N-iodo-succinimide; In N,N-dimethyl-formamide; at -30℃; for 1.5h; 4-Iodo-3-methoxy-1H-pyrazole A solution of 3-methoxy-1H-pyrazole (0.500 g, 5.10 mmol) in anhydrous DMF (8.00 mL) was cooled to -30 C. and charged with NIS (1.15 g, 5.10 mmol). The reaction mixture was stirred at -30 C. for 1.5 h. The reaction mixture was charged with H2O at -30 C. then the reaction was charged with EtOAc and separated. The aqueous was re-extracted with EtOAc (3*) and the combined organic fractions were washed with H2O (2*), 1M Na2S2O3 (1*), brine (1*), dried over Na2SO4, filtered and concentrated in vacuo resulting in the title compound as a light yellow solid. This material was taken on to the next step without further purification. 1H NMR (400 MHz, CD3OD): delta=3.88 (s, 3H), 7.50 (s, 1H). MS (ES+): m/z 225.04 [MH+]. HPLC: tR=2.97 min (polar-5 min, ZQ3).
  • 3
  • [ 1350325-05-1 ]
  • [ 627-18-9 ]
  • [ 1380307-48-1 ]
YieldReaction ConditionsOperation in experiment
56% Compound 48E: 3-(4-lodo-3-methoxy-1 H-pyrazol-1-yl)propan-1 -olA solution of 4-iodo-3(5)-methoxypyrazole (Compound 48F, 2 g, 8.92 mmol) in DMF (5.0 mL) was cooled to 0 C and NaH (386 mg) was added. After 45 minutes 3-bromopropanol (1.24 g, 8.92 mmol) was added. The reaction mixture was stirred at 0 C for 1.5 h and then at RT for 1 h. It was then poured into water (30 mL) and extracted with EtOAc (3 x 20mL). The combined organic layers were dried over Na2S04, filtered, concentrated and purified by column chromatography (Si02, ethyl acetate/hexanes, 1 :4) to yield 1 .4 g (56 %) of the desired product. 1H NMR (300 MHz, CDCI3) delta 7.24 (s, 1 H), 4.12 (t, J = 6.3 Hz, 2H), 3.92 (s, 3H), 3.64 (q, J = 5.7 Hz, 2H), 2.63 (t, J = 6 Hz, 1 H), 1.95-2.03 (m, 2H).
  • 4
  • benzene-1,3-dicarboxylic-5-boronic triacid [ No CAS ]
  • [ 1350325-05-1 ]
  • [ 147496-14-8 ]
  • C34H24N6O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
65% To a solution of 10 ml ofSchlek reaction tube (a glass instrument commonly used in anhydrous oxygenless operation) was added to 1.0 mmol of 2-bromo-5- (6-bromopyridine-3) pyridine, 2.1 mmol <strong>[1350325-05-1]3-methoxy-4-iodopyrazole</strong>, 0.03 mmol palladium acetate, 0.06 mmol dicyclohexyl (3,6-dimethyl(1,1'-biphenyl) -2-yl) phosphine, 5.0 mmol of potassium tert-butoxide, and 5 ml of dioxane, usingThe reaction vessel was purged with nitrogen for 3 times and then heated to 110 C with an oil bath under magnetic stirring. The reaction was refluxed for 24 hours. Down to room temperatureThe reaction solution was further added, 3.0 mmol of 3,5-dicarboxylbenzeneboronic acid, 0.02 mmol of palladium acetate, 0.05 mmol of 2'-dicyclohexyl2-I-propyl-4-sulfonate-1,1'-biphenyl sodium, 12.0 mmol of potassium carbonate, and 200 mmol of water;The mixture was heated to 100 C with an oil bath under magnetic stirring and the reaction was refluxed for 48 hours. Down to room temperature; add 20 ml of water, filter, with concentrated hydrochloric acidAdjust the filtrate PH to 1, room temperature stirring 6h, the filter, washed with ethanol, drying that product 14, yield 65%. this product(ESI) data for the compound (C34H24N6O10) was 676.18.
  • 5
  • benzene-1,3-dicarboxylic-5-boronic triacid [ No CAS ]
  • [ 1350325-05-1 ]
  • [ 263012-59-5 ]
  • C46H32N6O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% Under nitrogen protection,To a 10 ml Schlek reaction tube (a glass instrument commonly used in anhydrous oxygenless operation) was added 1.0 mmol(4-bromo-3-pyridyl) biphenyl, 2.2 mmol of <strong>[1350325-05-1]3-methoxy-4-iodopyrazole</strong>, 0.03 mmol of palladium acetate, 0.06 mmol of dicyclohexyl (3,6- 2 ', 4', 6'-triisopropyl (1,1'-biphenyl) -2-yl)6.0 mmol of potassium t-butoxide, and 5 ml of dioxane, and the reaction tube was purged with nitrogen three timesAnd then heated to 110 C with an oil bath under magnetic stirring and the reaction was refluxed for 24 hours. Down to room temperatureThe reaction solution was further added, 5.0 mmol of 3,5-dicarboxyphenylboronic acid, 0.03 mmol of palladium acetate,0.06 mmol 2'-dicyclohexyl-2,6-dimethoxy-3-sulfonic acid-1,1'-biphenyl sodium salt, 12.0 mmol potassium carbonate,And 100 mmol of water; then heated to 100 C with an oil bath under magnetic stirring and the reaction was refluxed for 48 hours.Down to room temperature; add 20 ml of water, filtration, with concentrated hydrochloric acid to adjust the pH of the filtrate to 1, room temperature stirring 6h,Filtered, washed with ethanol, dried product 28, yield 60%. The product (C46H32N6O10)Of the mass spectrum (ESI) data was 828.20.
  • 6
  • [ 1350325-05-1 ]
  • [ 25487-66-5 ]
  • 3,6-diiodo-1,2,4,5-tetrazine [ No CAS ]
  • C24H18N8O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
71% Under nitrogen protection,To a 10 ml Schlek reaction tube (a glass instrument commonly used in anhydrous oxygenless operation) was added 1.0 mmol3, 6-diiodetetrazine,2.1 mmol 3-Methoxy-4-iodopyrazole, 0.03 mmol palladium acetate,0.06 mmol di-tert-butyl (2 ', 4', 6'-triisopropyl-3,6-dimethoxybiphenyl-2-yl)5.0 mmol potassium tert-butoxide,And 5 ml of toluene, the reaction tube was replaced with nitrogen three times,And then heated to 110 C with an oil bath under magnetic stirring, and the reaction was refluxed for 20 hours. Down to room temperatureThe reaction solution was further added, 4.0 mmol of 3-carboxyphenylboronic acid, 0.02 mmol of palladium acetate, 0.05 mmol2'-dicyclohexylphosphino-2,6-di-I-propyl-4-sulfonate-1,1'-biphenyl sodium, 6.0 mmol of sodium carbonate,And 100 mmol of water; then heated to 100 C with an oil bath under magnetic stirring and the reaction was refluxed for 24 hours.Down to room temperature; add 20ml of water, filtration, with concentrated hydrochloric acid to adjust the pH of the filtrate to 1, room temperature after 5h,Filtered, washed with ethanol, dried to get the product 9, yield 71%. The product (C24H18N8O6)Of the mass spectrum (ESI) of 514.15.
  • 7
  • [ 1350325-05-1 ]
  • [ 149105-19-1 ]
  • C8H4I2N4 [ No CAS ]
  • C30H22N8O6 [ No CAS ]
YieldReaction ConditionsOperation in experiment
62% Under nitrogen protection,To a 10 ml Schlek reaction tube (a glass instrument commonly used in anhydrous oxygenless operation) was added 1.0 mmol2-iodo-5- (2-iodopyrimidine-3) pyrimidine 2.2 mmol of 3-methoxy-4-iodopyrazole, 0.02 mmol of palladium acetate,0.05 mmol dicyclohexyl (3,6-dimethoxy-2 ', 4', 6'-triisopropyl (1,1'-biphenyl) -2-yl)5.0 mmol of potassium t-butoxide, and 5 ml of dioxane, the reaction tube was purged with nitrogen three times,And then heated to 110 C with an oil bath under magnetic stirring, and the reaction was refluxed for 24 hours. Down to room temperatureThe reaction solution was further added, 4.0 mmol of <strong>[149105-19-1]2-carboxyphenylboronic acid</strong>, 0.03 mmol of palladium acetate, 0.06 mmol2-dicyclohexylphosphino-2,6-di-I-propyl-4-sulfonate-1,1'-biphenyl sodium, 10.0 mmol cesium carbonate,And 200 mmol of water; then heated to 100 C with an oil bath under magnetic stirring and the reaction was refluxed for 24 hours.Down to room temperature; add 20 ml of water, filtration, with concentrated hydrochloric acid to adjust the pH of the filtrate to 1, room temperature after 5h,Filtered, washed with ethanol, dried product 18, yield 62%. The product (C30H22N8O6)Of the mass spectrum (ESI) of 590.17.
  • 8
  • benzene-1,3-dicarboxylic-5-boronic triacid [ No CAS ]
  • [ 23229-26-7 ]
  • [ 1350325-05-1 ]
  • C28H20N6O10 [ No CAS ]
YieldReaction ConditionsOperation in experiment
72% Under nitrogen protection,To a 10 ml Schlek reaction tube (a glass instrument commonly used in anhydrous oxygenless operation) was added 1.0 mmol 2, 5-dibromopyrazine, 2.2 mmol <strong>[1350325-05-1]3-methoxy-4-iodopyrazole</strong>, 0.05 mmol palladium acetate, 0.08 mmolDicyclohexyl (3,6-dimethoxy-2 ', 4', 6'-triisopropyl (1,1'-biphenyl) -2-yl)6.0 mmol potassium tert-butoxide,And 5 ml of toluene, the reaction tube was purged with nitrogen three times and then heated to 110 C with an oil bath under magnetic stirring,The reaction was refluxed for 24 hours. To the room temperature; add to the reaction solution, 5.0 mmol3,5-dicarboxybenzeneboronic acid,0.03 mmol of palladium acetate, 0.05 mmol of 2'-dicyclohexyl-2,6-dimethoxy-3-sulfonic acid-1,1'-biphenyl sodium salt, 12.0 mmol of potassium carbonate, and 200 mmol of water; The mixture was heated to 100 C with an oil bath under stirring and the reaction was refluxed for 48 hours. Go to room temperature; add 20ml water, filter, with concentrated hydrochloric acid to adjust the pH of the filtrate to 1, room temperature stirring 6h, filtration, washing with ethanol, drying product 5, yield 72%. The mass spectrum (ESI) of the product (C28H20N6O10) was 600.12
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