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[ CAS No. 1003043-55-7 ] {[proInfo.proName]}

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Chemical Structure| 1003043-55-7
Chemical Structure| 1003043-55-7
Structure of 1003043-55-7 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1003043-55-7 ]

CAS No. :1003043-55-7 MDL No. :MFCD07375134
Formula : C6H9BN2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :VTPBKJXRYUDPAJ-UHFFFAOYSA-N
M.W : 167.96 Pubchem ID :16427142
Synonyms :

Calculated chemistry of [ 1003043-55-7 ]

Physicochemical Properties

Num. heavy atoms : 12
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 3
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 43.16
TPSA : 75.47 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) : -7.48 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : -0.22
Log Po/w (WLOGP) : -1.44
Log Po/w (MLOGP) : -1.62
Log Po/w (SILICOS-IT) : -1.36
Consensus Log Po/w : -0.93

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.91
Solubility : 20.4 mg/ml ; 0.122 mol/l
Class : Very soluble
Log S (Ali) : -0.91
Solubility : 20.8 mg/ml ; 0.124 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.07
Solubility : 14.3 mg/ml ; 0.0853 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.22

Safety of [ 1003043-55-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1003043-55-7 ]

* 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 [ 1003043-55-7 ]

[ 1003043-55-7 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 1003043-55-7 ]
  • [ 1417184-45-2 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; Example 283 7-(2-Ethoxy-pyrimidin-5-yl)-2-(2-quinolin-2-yl-ethyl)-2,3-dihydro-isoindol-1-one The title compound was prepared in analogy to the process described in Example 281 using <strong>[1003043-55-7]2-ethoxypyrimidin-5-ylboronic acid</strong> (16.7 mg, 0.1 mmol) dissolved in dioxane (0.3 mL) instead of 5-cyanothiophen-2-ylboronic acid (15.3 mg, 0.1 mmol) dissolved in dioxane (0.3 mL). Yield: 10 mg, 29%. 1H NMR (400 MHz, DMSO/D2O) delta ppm 8.59 (s, 2H) 8.29 (d, J=8.54 Hz, 1H) 7.83-7.96 (m, 2H) 7.62-7.74 (m, 3H) 7.53-7.58 (m, 1 H) 7.49 (d, J=8.54 Hz, 1H) 7.42-7.46 (m, 1H) 4.55 (s, 2H) 4.37-4.44 (m, 2H) 3.98 (t, J=7.17 Hz, 2H) 3.28 (t, J=7.17 Hz, 2H) 1.37 (t, J=7.02 Hz, 3H); MS (ESI) m/z 411 (M+H)+.
  • 2
  • [ 1003043-55-7 ]
  • [ 1417185-07-9 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; Example 327 4-(2-Ethoxy-pyrimidin-5-yl)-6-(2-quinolin-2-yl-ethyl)-6,7-dihydro-pyrrolo[3,4-b]pyridin-5-one The title compound was prepared in analogy to the process described in Example 322 but using <strong>[1003043-55-7]2-ethoxypyrimidin-5-ylboronic acid</strong> (16.8 mg, 0.1 mmol) dissolved in dioxane (0.35 mL) instead of 3-methylpyridin-4-ylboronic acid (13.7 mg, 0.1 mmol) dissolved in dioxane (0.35 mL). Yield: 2.7 mg, 8%. 1H NMR (500 MHz, DMSO/D2O) delta ppm 8.75-8.79 (m, 3H) 8.29 (d, J=8.24 Hz, 1H) 7.94 (d, J=7.02 Hz, 1H) 7.82 (d, J=8.54 Hz, 1H) 7.68-7.73 (m, 1H) 7.49-7.57 (m, 3H) 4.61 (s, 2H) 4.43 (q, J=7.02 Hz, 2H) 4.03 (t, J=7.17 Hz, 2H) 3.31 (t, J=7.17 Hz, 2H) 1.37 (t, J=7.02 Hz, 3H); MS (ESI) m/z 412 (M+H)+.
  • 3
  • [ 1003043-55-7 ]
  • [ 1417185-23-9 ]
YieldReaction ConditionsOperation in experiment
In 1,4-dioxane; Example 343 4-(2-Ethoxy-pyrimidin-5-yl)-2-(2-quinolin-2-yl-ethyl)-2,3-dihydro-isoindol-1-one The title compound was prepared in analogy to the process described in Example 341 but using <strong>[1003043-55-7]2-ethoxypyrimidin-5-ylboronic acid</strong> (16.8 mg, 0.1 mmol) dissolved in dioxane (0.35 mL) instead of 2-(dimethylamino)pyrimidin-5-ylboronic acid (16.7 mg, 0.1 mmol) dissolved in dioxane (0.35 mL). Yield: 3.2 mg, 9%. 1H NMR (500 MHz, DMSO/D2O) delta ppm 8.85 (s, 2H) 8.28 (d, J=8.24 Hz, 1H) 7.91 (dd, J=15.41, 8.09 Hz, 2 H) 7.69-7.76 (m, 3H) 7.63 (t, J=7.48 Hz, 1H) 7.54-7.59 (m, 1H) 7.51 (d, J=8.24 Hz, 1H) 4.76 (s, 2H) 4.45 (q, J=7.02 Hz, 2H) 4.02 (t, J=7.32 Hz, 2H) 3.30 (t, J=7.32 Hz, 2H) 1.39 (t, J=7.02 Hz, 3H); MS (ESI) m/z 411 (M+H)+. MS (APCI) m/z 411 (M+H)+.
  • 4
  • [ 1003043-55-7 ]
  • [ 1612171-85-3 ]
  • [ 1612164-64-3 ]
YieldReaction ConditionsOperation in experiment
18% With bis(di-tert-?butyl(4-?dimethylaminophenyl)?phosphine)?dichloropalladium(II); sodium carbonate; In acetonitrile; at 140.0℃; for 0.333333h;Inert atmosphere; Microwave irradiation; To a glass vial was added 2-methoxypyrimidine-5-boronic acid (0.105 g, 0.613 mmol), (2- chloropyrimidin-4-yl)-(l-isopropyl-lH-imidazo[4,5-c]pyridin-6-yl)amine (Example 12, Step 4) (0.176 mg, 0.613 mmol), Pd(Amphos)2Cl2 (22 mg, 0.031 mmol), a 2M solution of Na2C03 (0.46 mL, 0.92 mmol) and acetonitnle (2.5 mL). The mixture was degassed by nitrogen bubbling for 20 min. The reaction vial was sealed and heated in a microwave at 140 C for 20 min. Alternatively, the reaction was sealed and stirred at 100 C in an oil bath for 2 h. The reaction mixture was cooled to room temperature, filtered and concentrated. The crude product was purified by reverse- phase HPLC and lyophilized to give the title compound (41 mg, 18%). LCMS (ESI): RT 3.91 min, [M+H]+ 377.2, method = B; lH NMR (400 MHz, DMSO-d6) delta 10.31 (s, 1H), 9.40 (s, 2H), 8.73 (d, J= 1.0 Hz, 1H), 8.46 (d, J= 5.9 Hz, 1H), 8.39 (d, J= 7.9 Hz, 2H), 7.30 (s, 1H), 4.85 - 4.71 (m, 1H), 4.46 (q, J= 7.1 Hz, 2H), 1.61 (d, J= 6.8 Hz, 6H), 1.38 (t, J= 7.1 Hz, 3H).
  • 5
  • [ 1003043-55-7 ]
  • 2-(3-dimethylaminomethyl-5-methyl[1,2,4]triazol-1-yl)-1-{(R)-4-[4-(2-ethoxypyrimidin-5-yl)-2-trifluoromethylthiazol-5-yl]-2-methylpiperazin-1-yl}ethanone [ No CAS ]
  • 6
  • [ 1003043-55-7 ]
  • 2-ethoxy-5-[5-((R)-3-methylpiperazin-1-yl)-2-trifluoromethylthiazol-4-yl]pyrimidine [ No CAS ]
  • 7
  • [ 1003043-55-7 ]
  • 1-{(R)-4-[4-(2-ethoxypyrimidin-5-yl)-2-trifluoromethylthiazol-5-yl]-2-methylpiperazin-1-yl}-2-(5-ethyl-3-methyl[1,2,4]triazol-1-yl)ethanone [ No CAS ]
  • 8
  • [ 1003043-55-7 ]
  • (R)-4-(4-bromo-2-trifluoromethylthiazol-5-yl)-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
  • (R)-4-[4-(2-ethoxypyrimidin-5-yl)-2-trifluoromethylthiazol-5-yl]-2-methylpiperazine-1-carboxylic acid tert-butyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
1.35 g With bis-triphenylphosphine-palladium(II) chloride; sodium carbonate; In acetonitrile; at 80.0℃;Inert atmosphere; A mixture of intermediate 17.7 (1 .63g), <strong>[1003043-55-7]2-ethoxypyrimidine-5-boronic acid</strong> (778mg), Pd(PPh3)2CI2 (152mg), 1 M Na2C03 (12mL) in MeCN (12mL) was vigorously stirred at 80C under argon overnight. The reaction mixture was allowed to cool down to RT, diluted with H20 and extracted with DCM (3x). The combined org. layers were dried over MgS04, filtrated off and evaporated to dryness. The crude was purified by CC (Biotage, SNAP 50g cartridge, solvent A: Hep; solvent B: EA; gradient in %B: 10 for 5CV, 10 to 30 over 5CV, 30 for 3CV) to afford 1.35g as pale yellow resin. LC-MS (B): tR = 1 .04min; [M+H]+: 473.9.
  • 9
  • [ 1003043-55-7 ]
  • ethyl 3-bromo-5-(trifluoromethoxy)-1H-indole-2-carboxylate [ No CAS ]
  • C18H16F3N3O4 [ No CAS ]
  • 10
  • [ 1003043-55-7 ]
  • 8-bromo-9-(4-[[(3S)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxy]-phenyl)-6,7-dihydro-5H-benzo[7]annulen-3-ol [ No CAS ]
  • 6-(2-ethoxypyrimidin-5-yl)-5-[4-[(3S)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7H-benzo[7]annulen-2-ol [ No CAS ]
YieldReaction ConditionsOperation in experiment
57.7% With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; caesium carbonate; In 1,4-dioxane; water; at 72.0℃; for 1.0h; To a solution of 8-bromo-9-(4-[(3S)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxy}phenyl)-6,7-dihydro-5H-benzo[7]annulen-3-ol (D4) (74.9 mg, 162.69 mumol), in dioxane (1 ml) and water (0.5 ml), was added <strong>[1003043-55-7]2-ethoxypyrimidin-5-yl boronic acid</strong> (30.06 mg, 178.96 mumol), Cs2CO3(106.12 mg, 325.38 mumol), and Pd(dppf)Cl2 (7.97 mg, 9.76 mumol). The reaction mixture was heated at 72 C. for 1 hour, partitioned between water and DCM and phases separated on hydrophobic partition column. The organic solvents were concentrated under reduced pressure and the residue was purified by column chromatography eluting with a gradient of MeOH in DCM (0% to 10%) to give a solid which was further purified on strong cation exchange (SCX) column to give 47.3 mg (57.7%) of 6-(2-ethoxypyrimidin-5-yl)-5-[4-[(3S)-1-(3-fluoropropyl)pyrrolidin-3-yl]oxyphenyl]-8,9-dihydro-7H-benzo[7]annulen-2-01.
  • 11
  • [ 1003043-55-7 ]
  • C14H11BrN2O2S [ No CAS ]
  • C20H18N4O3S [ No CAS ]
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