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[ CAS No. 1493764-08-1 ] {[proInfo.proName]}

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Chemical Structure| 1493764-08-1
Chemical Structure| 1493764-08-1
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Product Details of [ 1493764-08-1 ]

CAS No. :1493764-08-1 MDL No. :MFCD28142814
Formula : C25H33N7O2 Boiling Point : -
Linear Structure Formula :- InChI Key :NPVXOWLPOFYACO-UHFFFAOYSA-N
M.W : 463.58 Pubchem ID :71721525
Synonyms :
Chemical Name :N-(4-(1H-Imidazol-1-yl)benzyl)-2-(butylamino)-4-((trans-4-hydroxycyclohexyl)amino)pyrimidine-5-carboxamide

Calculated chemistry of [ 1493764-08-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 34
Num. arom. heavy atoms : 17
Fraction Csp3 : 0.44
Num. rotatable bonds : 11
Num. H-bond acceptors : 5.0
Num. H-bond donors : 4.0
Molar Refractivity : 132.75
TPSA : 116.99 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : No
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.42 cm/s

Lipophilicity

Log Po/w (iLOGP) : 3.89
Log Po/w (XLOGP3) : 3.81
Log Po/w (WLOGP) : 2.99
Log Po/w (MLOGP) : 1.64
Log Po/w (SILICOS-IT) : 2.25
Consensus Log Po/w : 2.92

Druglikeness

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

Water Solubility

Log S (ESOL) : -4.76
Solubility : 0.00808 mg/ml ; 0.0000174 mol/l
Class : Moderately soluble
Log S (Ali) : -5.96
Solubility : 0.000506 mg/ml ; 0.00000109 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -7.3
Solubility : 0.0000231 mg/ml ; 0.0000000499 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.29

Safety of [ 1493764-08-1 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P301+P312+P330 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 1493764-08-1 ]

* 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 [ 1493764-08-1 ]

[ 1493764-08-1 ] Synthesis Path-Downstream   1~6

YieldReaction ConditionsOperation in experiment
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; 2-(Butylamino)-N-(4-fluorobenzyl)-4-(((trans-4-hvdroxycyclohexyl)amino)pyrimidine-5-carboxamide General procedure: A mixture of methyl 2-(butylamino)-4-(((trans-4-hydroxycyclohexyl)amino) pyrimidine-5-carboxylate (682.6 mg, 2.12 mmol) and lithium hydroxide monohydrate (888.4 mg, 21.2 mmol) in a mixture of methanol and water (25 mL, 3 :2, v/v) was heated at reflux for 2h. Then the reaction mixture was cooled to room temperature and acidified by a 4. ON solution of HCl (4N) to PH 3. The resulting mixture was extracted with EtOAc (4x). The combined organic layers were dried (Na2SO4) and concentrated to provide 2-(butylamino)-4- (((1r,4r)-4-hydroxycyclohexyl)amino)pyrimidine-5-carboxylic acid(647.1 mg, 99%), which was used in the next step without further purifications. MS m/z 309.30 [M+H]+. A solution of the acid (61 mg, 0.20 mmol), O-(benzotizol-1-yl)-N,N,N'N'- tetramethyluronium tetrafluoroborate (TBTU, 81.4 mg, 0.25 mmol, 1.3 eq) and N,N- diisopropylethylamine (DIEA, 77.5 mg, 0.60 mmol, 3.0 eq) in anhydrous DMF (3.0 mL) and was added 4-fluorobenzylamine (37.5 mg, 0.30 mmol, 1.5eq) in DMF (1.0 mL) dropwisely at room temperature. The resulting mixture was stirred for overnight, then diluted with EtOAc (15 mL) and washed with water (3x). The organic layer was dried (Na2SO4) and concentrated. The residue was purified on HPLC to give the title compound (61.5 mg, 74%) as a yellow solid. 1H NMR (400 MHz, CDCl3) S 9.57 (d, J = 7.4 Hz, 1H), 8.77 (s, 1H), 8.13 (s, 1H), 7.40-7.31 (m, 1H), 7.29-7.22 (m, 3H), 7.00 (t, J = 8.6 Hz, 2H), 4.44 (d, J = 5.2 Hz, 2H), 4.00 (s, 1H), 3.77-3.62 (m, 1H), 3.40 (dd, J = 13.0, 6.9 Hz, 2H), 2.15-2.09 (m, 2H), 2.04 (d, J= 7.6 Hz, 2H), 1.66-1.54 (m, 2H), 1.49-1.33 (m, 6H), 0.94 (t, J= 7.3 Hz, 3H); MS m/z 416.30 [M+H]+.
With O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20℃; 3 General procedure: A solution of the acid (61 mg, 0.20 mmol), O-(benzotriazol-l-yl)-N,jV,N' N1- tetramethyluronium tetrafluoroborate (TBTU, 81.4 mg, 0.25 mmol, 1.3 eq) and N,N- diisopropylethylamine (DIEA, 77.5 mg, 0.60 mmol, 3.0 eq) in anhydrous DMF (3.0 mL) and was added 4-fluorobenzylamine (37.5 mg, 0.30 mmol, 1.5eq) in DMF (1.0 mL) dropwisely at room temperature. The resulting mixture was stirred for overnight, then diluted with EtOAc (15 mL) and washed with water (3 ). The organic layer was dried (Na2S04) and concentrated. The residue was purified on HPLC to give the title compound (61.5 mg, 74%) as a yellow solid. 1H NM (400 MHz, CDC13) <5 9.57 (d, J= 7.4 Hz, 1H), 8.77 (s, lH), 8.13 (s, 1H), 7.40-7.31 (m, 1H), 7 '.29-7.22 (m, 3H), 7.00 (t, J= 8.6 Hz, 2H), 4.44 (d, J= 5.2 Hz, 2H), 4.00 (s, 1H), 3.77-3.62 (m, 1H), 3.40 (dd, J = 13.0, 6.9 Hz, 2H), 2.15-2.09 (m, 2H), 2.04 (d, J= 7.6 Hz, 2H), 1.66-1.54 (m, 2H), 1.49-1.33 (m, 6H), 0.94 (t, J= 7.3 Hz, 3H); MS m/z 416.30 [M+H]+.
  • 2
  • [ 3177-20-6 ]
  • 2-(butylamino)-4-[(4-hydroxycyclohexyl)amino]-N-[4-(1H-imidazol-1-yl)phenyl]methyl}pyrimidine-5-carboxamide [ No CAS ]
  • 3
  • [ 1497419-93-8 ]
  • [ 1493764-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 3 h / 20 °C 2: lithium hydroxide monohydrate / water / 2 h / Reflux 3: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 20 °C
  • 4
  • [ 1493764-36-5 ]
  • [ 1493764-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: lithium hydroxide monohydrate / water / 2 h / Reflux 2: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 20 °C
  • 6
  • [ 2972-52-3 ]
  • [ 1493764-08-1 ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 5 steps 1: N-ethyl-N,N-diisopropylamine / dichloromethane / 1 h / 0 °C 2: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 1.5 h / 0 °C 3: N-ethyl-N,N-diisopropylamine / isopropyl alcohol / 3 h / 20 °C 4: lithium hydroxide monohydrate / water / 2 h / Reflux 5: N-ethyl-N,N-diisopropylamine; O-(benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium tetrafluoroborate / N,N-dimethyl-formamide / 20 °C
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