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[ CAS No. 1201643-90-4 ] {[proInfo.proName]}

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Chemical Structure| 1201643-90-4
Chemical Structure| 1201643-90-4
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Product Details of [ 1201643-90-4 ]

CAS No. :1201643-90-4 MDL No. :MFCD16036118
Formula : C6H11BN2O2 Boiling Point : -
Linear Structure Formula :- InChI Key :VLVZNLMUFJYZDG-UHFFFAOYSA-N
M.W : 153.98 Pubchem ID :53216602
Synonyms :

Calculated chemistry of [ 1201643-90-4 ]

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 5
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 42.93
TPSA : 58.28 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) : -7.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.16
Log Po/w (WLOGP) : -0.86
Log Po/w (MLOGP) : -1.01
Log Po/w (SILICOS-IT) : -1.77
Consensus Log Po/w : -0.76

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.9
Solubility : 19.5 mg/ml ; 0.126 mol/l
Class : Very soluble
Log S (Ali) : -0.61
Solubility : 37.9 mg/ml ; 0.246 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.11
Solubility : 120.0 mg/ml ; 0.78 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.09

Safety of [ 1201643-90-4 ]

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 [ 1201643-90-4 ]

* 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 [ 1201643-90-4 ]

[ 1201643-90-4 ] Synthesis Path-Downstream   1~16

  • 1
  • [ 1201643-90-4 ]
  • [ 1292267-81-2 ]
  • [ 1292267-58-3 ]
YieldReaction ConditionsOperation in experiment
With tetrakis(triphenylphosphine) palladium(0); sodium carbonate In 1,4-dioxane; water at 120℃; Microwave irradiation;
  • 2
  • [ 1201643-90-4 ]
  • [ 857003-04-4 ]
  • [ 1362160-31-3 ]
YieldReaction ConditionsOperation in experiment
45% With potassium carbonate In dimethyl sulfoxide 4Å molecular sieves;
With copper diacetate In dimethyl sulfoxide at 60℃; for 16h; Alkaline conditions;
With copper diacetate In dimethyl sulfoxide at 60℃; for 16h; Alkaline conditions;
  • 4
  • [ 1201643-90-4 ]
  • [ 1450723-31-5 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 4 steps 1: copper diacetate / dimethyl sulfoxide / 16 h / 60 °C / Alkaline conditions 2: hydrogenchloride / water; isopropyl alcohol / Reflux 3: toluene / 2 h / 110 °C 4: ethanol / 2 h / Reflux
  • 6
  • [ 1201643-90-4 ]
  • [ 1450724-13-6 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: copper diacetate / dimethyl sulfoxide / 16 h / 60 °C / Alkaline conditions 2: hydrogenchloride / water; isopropyl alcohol / Reflux 3: toluene / 2 h / 110 °C
  • 8
  • [ 1201643-90-4 ]
  • [ 1586044-82-7 ]
  • [ 1586040-92-7 ]
YieldReaction ConditionsOperation in experiment
256 5-amino-N-(5-((2S,5R,6R)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(1-isopropyl-1H-pyrazol-4-yl)thiazole-4-carboxamide 256 Example 256 5-amino-N-(5-((2S,5R,6R)-5-amino-6-fluorooxepan-2-yl)-1-methyl-1H-pyrazol-4-yl)-2-(1-isopropyl-1H-pyrazol-4-yl)thiazole-4-carboxamide 256 Following the procedure for Example 101 starting from tert-butyl N-[2-bromo-4-[[5-[(2S,5R,6R)-5-(tert-butoxycarbonylamino)-6-fluoro-oxepan-2-yl]-1-methyl-pyrazol-4-yl]carbamoyl]thiazol-5-yl]carbamate (Intermediate 88), and replacing 3,6-dihydro-2H-pyran-4-boronic acid pinacol ester with (1-isopropyl-1H-pyrazol-4-yl)boronic acid gave 256. 1H NMR (400 MHz, DMSO-d6) δ 9.37 (s, 1H), 8.15 (s, 1H), 7.83 (s, 1H), 7.77 (s, 1H), 7.25 (s, 2H), 5.12-4.80 (m, 2H), 4.60-4.45 (m, 1H), 4.18-3.95 (m, 2H), 3.72 (s, 3H), 3.38-3.26 (m, 1H), 2.33-2.22 (m, 1H), 1.83-1.56 (m, 5H), 1.44 (d, J=6.7 Hz, 6H). LCMS (ES+) m/z 463 (M+1).
  • 9
  • [ 1201643-90-4 ]
  • [ 1439878-56-4 ]
  • N-(2,5-difluoro-4-((2-(1-isopropyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)phenyl)-4-ethoxy-1-(4-fluorophenyl)-2-oxo-1,2-dihydropyridine-3-carboxamide [ No CAS ]
YieldReaction ConditionsOperation in experiment
69% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In 1,4-dioxane; water at 80℃; for 5h; Inert atmosphere; 6 Example 6: Example 6: Example A6 (200 mg, 0.388 mmol), (i-isopropyl-1H-pyrazol-4-yl)boronic acid (72 mg, 0.465 mmol) and K2C03 (161 mg, 1.163 mmol) were combined in dioxane (4 mL) and H20 (2 mL), sparged with Ar, treated with Pd(PPh3)4 (22 mg, 19 jimol) and heated at 80°C for 5 h. The mixture was cooled to RT, treated with EtOAc and H20, filtered through diatomaceous earth and the layers of the filtrate separated. The organic layer was washed with brine, dried over Na2504, concentrated to dryness and purified via silica gel chromatography (EtOAc/Hex) to afford N-(2,5 -difluoro-4-((2-( 1 -isopropyl- 1 H-pyrazol-4-yl)pyridin-4-yl)oxy)phenyl)-4-ethoxy- 1 -(4-fluorophenyl)-2-oxo- 1 ,2-dihydropyridine-3 -carboxamide (159 mg, 69%) as a white solid. ‘HNMR(400 MHz, DMSO-d6): ö 11.19 (s, 1H), 8.38-8.32 (m, 3 H), 7.99 (s, 1 H), 7.92 (d, J = 7.8 Hz, 1 H), 7.53-7.46 (m, 3 H), 7.36 (m, 2H), 7.29 (d, J = 2.5 Hz, 1 H), 6.71 (dd, J = 5.7, 2.4 Hz, 1 H), 6.55 (d, J = 7.9 Hz, 1 H), 4.50(m, 1 H), 4.28 (q, J = 7.0 Hz, 2 H), 1.42 (d, J = 6.7 Hz, 6 H), 1.33 (t, J = 7.0 Hz, 3 H); MS(ESI) mlz: 590.2 (M+Hj.
  • 10
  • [ 15864-32-1 ]
  • [ 1201643-90-4 ]
  • C13H14N4S [ No CAS ]
YieldReaction ConditionsOperation in experiment
With Pd-118 In water; acetonitrile at 80 - 100℃; Microwave irradiation;
  • 11
  • [ 1201643-90-4 ]
  • 4-((2-((6-chloropyridin-3-yl)methyl)-3-oxo-2,3-dihydro-1H-isoindol-4-yl)oxy)-3,5-difluorobenzonitrile [ No CAS ]
  • 3,5-difluoro-4-((2-((6-(1-isopropyl-1H-pyrazol-4-yl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydro-1H-isoindol-4-yl)oxy)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.079 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere; 382 Example 382 3,5-difluoro-4-((2-((6-(1-isopropyl-1H-pyrazol-4-yl)pyridin-3-yl)methyl)-3-oxo-2,3-dihydro-1H-isoindol-4-yl)oxy)benzonitrile To a solution of (6-chloropyridin-3-yl)methanamine (0.22 g) and ethyl 2-(bromomethyl)-6-(4-cyano-2,6-difluorophenoxy)benzoate (0.50 g) obtained in Reference Example 231 in THF (10 mL) was added potassium carbonate (0.52 g), and the mixture was stirred under an argon atmosphere at room temperature for 3 days. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue were collected by filtration, and washed with ethyl acetate. To a solution of the obtained residue (0.20 g), (1-isopropyl-1H-pyrazol-4-yl)boronic acid (0.090 g) and 2M aqueous sodium carbonate solution (0.49 mL) in DME (4 mL) was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.036 g), and the mixture was stirred under an argon atmosphere at 80°C overnight. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was purified by silica gel chromatography (hexane-ethyl acetate), and solidified with ethyl acetate to give the title compound (0.079 g). MS: [M+H]+ 486.2 1H NMR (300 MHz, CDCl3) δ 1.56 (6H, d, J = 6.8 Hz), 4.31 (2H, s), 4.55 (1H, quin, J = 6.7 Hz), 4.75 (2H, s), 6.84 (1H, d, J = 8.1 Hz), 7.18 (1H, d, J = 7.6 Hz), 7.35 (2H, d, J = 7.0 Hz), 7.42-7.50 (2H, m), 7.65 (1H, dd, J = 8.1, 2.3 Hz), 7.95 (1H, s), 8.01 (1H, s), 8.50 (1H, d, J = 2.1 Hz).
  • 12
  • [ 1201643-90-4 ]
  • C21H12BrF2N3O2 [ No CAS ]
  • 3,5-difluoro-4-((2-(4-(1-isopropyl-1H-pyrazol-4-yl)benzyl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-4-yl)oxy)benzonitrile [ No CAS ]
YieldReaction ConditionsOperation in experiment
0.0041 g With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; sodium carbonate In 1,2-dimethoxyethane; water at 80℃; Inert atmosphere; 384 Example 384 3,5-difluoro-4-((2-(4-(1-isopropyl-1H-pyrazol-4-yl)benzyl)-3-oxo-2,3-dihydro-1H-pyrrolo[3,4-c]pyridin-4-yl)oxy)benzonitrile A solution of ethyl 2-(4-cyano-2,6-difluorophenoxy)-4-formylnicotinate (0.30 g) obtained in Reference Example 229 and (4-bromophenyl)methanamine (0.19 g) in THF (6 mL) was stirred at room temperature for 4 hr. The reaction mixture was concentrated, to a solution of the residue in acetic acid (6 mL) was added sodium triacetoxyhydroborate (0.29 g) at room temperature, and the mixture was stirred under an argon atmosphere at room temperature for 2 hr. The reaction mixture was neutralized with saturated aqueous sodium hydrogen carbonate solution, and the mixture was diluted with ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated. To a solution of the obtained residue (0.15 g), (1-isopropyl-1H-pyrazol-4-yl)boronic acid (0.056 g) and 2M aqueous sodium carbonate solution (0.49 mL) in DME (3 mL) was added [1,1-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (0.024 g), and the mixture was stirred under an argon atmosphere at 80°C overnight. The reaction mixture was diluted with water and ethyl acetate. The organic layer was separated, washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was crudely purified by silica gel chromatography (hexane-ethyl acetate), and further purified by reversed-phase preparative HPLC (water-0.1% TFA acetonitrile). The residue was solidified with ethyl acetate to give the title compound (0.0041 g). MS: [M+H]+ 486.2 1H NMR (300 MHz, CDCl3) δ 1.54-1.58 (6H, m), 4.35 (2H, s), 4.54 (1H, quin, J = 6.7 Hz), 4.81 (2H, s), 7.16 (1H, d, J = 5.1 Hz), 7.32-7.39 (4H, m), 7.45-7.51 (2H, m), 7.67 (1H, s), 7.77 (1H, s), 8.15 (1H, d, J = 5.1 Hz).
  • 13
  • [ 1007110-00-0 ]
  • [ 1201643-90-4 ]
  • tert-butyl (2S)-2-[(S)-hydroxy{3-[1-(propan-2-yl)-1H-pyrazol-4-yl]phenyl}methyl]piperidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
100% With tetrakis(triphenylphosphine) palladium(0); potassium carbonate In ethanol; N,N-dimethyl-formamide for 1.5h; Heating; tert-Butyl (2S)-2-{(S)-Hydroxy[4-(pyridin-3-yl)phenyl]-methyl}piperidine-1-carboxylate (20a) General procedure: 3-Pyridineboronicacid (2.50 g, 20.3 mmol), potassium carbonate (2.84 g,20.5 mmol), and tetrakis(triphenylphosphine) palladium(0)(0.47 g, 0.41 mmol) were added to a solution of 19a (6.00 g,13.7 mmol) in a mixed solvent of DMF-EtOH (2 : 1, 135 mL)were added, and the mixture was stirred at 90°C for 1.5 h. Thereaction mixture was partitioned between water and EtOAc,and the organic layer was washed with water and brine, driedover anhydrous MgSO4, filtered, and concentrated in vacuo.The residue was purified using NH-silica gel column chromatography(33-50% EtOAc in hexane) to yield 20a (4.40 g,87%) as a pale yellow powder.
  • 14
  • [ 1201643-90-4 ]
  • C19H15ClFN3O3 [ No CAS ]
  • C25H24FN5O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With tris-(dibenzylideneacetone)dipalladium(0); potassium carbonate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene In 1,4-dioxane; water at 110℃; for 1h; Inert atmosphere; 61 Synthesis of compound 56.4 General procedure: Synthesis of compound 56.4. To a mixture of 4.1 (0.140g, 0.374mmol, 1.0 eq) in 1,4- dioxane (3.0 ml) was added 56.3 (0.055g, 0.29mmol, l.Oeq) and K2C03 (0.129g, 0.936mmol, 2.5eq). The reaction mixture was degassed for 10 min. under argon atmosphere, then Pd2(dba)3 (0.034g, 0.037mmol, 0. leq) and Xantphos (0.043g, 0.074mmol, 0.2eq) were added and again degassed for 5 minutes. The reaction was stirred at 100 °C for 4h. Upon completion of the reaction, reaction mixture was transferred into water and product was extracted with EtOAc. Organic layers were combined, washed with brine solution, dried over Na2S04 and concentrated under reduced pressure to obtain the crude which was purified by column chromatography to furnish 56.4 (0.080g, 41.9%). MS(ES): m/z 519.5 [M+H]+.
  • 15
  • [ 1201643-90-4 ]
  • (S)-7-chloro-3-(2,3-difluorophenyl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazine [ No CAS ]
  • (S)-3-(2,3-difluorophenyl)-7-(1-isopropyl-1H-pyrazol-4-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazine [ No CAS ]
YieldReaction ConditionsOperation in experiment
33% With chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II); potassium carbonate In water; N,N-dimethyl-formamide at 110℃; for 1h; 46.2 Step 2. (S)-3-(2,3-Difluorophenyl)-7-(1-isopropyl-1H-pyrazol-4-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazine A sample of (S)-7-chloro-3-(2,3-difluoro phenyl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazine (30 mg, 0.085 mmol) was dissolved in DMF (0.95 ml) and water (0.19 ml). This solution was treated with (1-isopropyl-1H-pyrazol-4-yl)boronic acid (39 mg, 0.26 mmol) and K2CO3 (35 mg, 0.26 mmol). Pd XPhos G2 (10 mg, 0.013 mmol) was added, the vial was capped, and the solution was stirred at 110° C. After 1 hour, LCMS indicated consumption of the starting material. The solution was cooled to room temperature, diluted with MeCN and water, filtered through a SiliaPrep Thiol cartridge, and purified by HPLC (pH=2 method) to provide (S)-3-(2,3-difluorophenyl)-7-(1-isopropyl-1H-pyrazol-4-yl)-6-((tetrahydrofuran-3-yl)oxy)imidazo[1,2-b]pyridazine (12 mg, 0.028 mmol, 33% yield). LCMS calculated for C22H22F2N5O2(M+H)+: m/z 426.2; found: 426.2.
  • 16
  • [ 1201643-90-4 ]
  • 8-amino-5-bromo-2-cyclohexyl-3,4-dihydro-2,7-naphthyridin-1(2H)-one [ No CAS ]
  • 8-amino-2-cyclohexyl-5-(1-isopropyl-1H-pyrazol-4-yl)-3,4-dihydro-2,7-naphthyridin-1(2H)-one [ No CAS ]
YieldReaction ConditionsOperation in experiment
60% With potassium phosphate; chloro(2-dicyclohexylphosphino-2’,4’,6’-triisopropyl-1,1‘-biphenyl)[2-(2’-amino-1,1‘-biphenyl’)]palladium(II) In 1,4-dioxane; water at 90℃; for 12h; Inert atmosphere; Sealed tube; General Procedure E for Synthesis of Inhibitors 9-12: General procedure: Aminopyridine 8, the indicated boronate or boronic acid (3.0 equiv, see Scheme S2),2 Xphos Pd G2 (20 mol %), and potassium phosphate tribasic (3.2 equiv) were combined in a small vial with a mixture of 1,4-dioxane and water (5:1, 0.09 M). The solution was degassed with nitrogen, then the vial was sealedand heated to 90 C, with stirring, for 12 h. After cooling to 23 C, the reaction mixture was filtered, thenthe filtrate was concentrated. For boronates and boronic acids A-J, O, and P, the residue was directlypurified by preparative LC in the below indicated yields (Scheme S2). For pinacol boronates K-N, theresidue was dissolved in 1:1 dichloromethane/trifluoracetic acid, stirred for 30 minutes at 23 C,concentrated, then purified by preparative LC in the below indicated yields (Scheme S2).
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