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[ CAS No. 929095-18-1 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 929095-18-1
Chemical Structure| 929095-18-1
Structure of 929095-18-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 929095-18-1 ]

CAS No. :929095-18-1 MDL No. :MFCD12755419
Formula : C27H28F3N5O2S Boiling Point : -
Linear Structure Formula :- InChI Key :ZHJGWYRLJUCMRT-QGZVFWFLSA-N
M.W : 543.60 Pubchem ID :15983966
Synonyms :
GSK461364A

Calculated chemistry of [ 929095-18-1 ]

Physicochemical Properties

Num. heavy atoms : 38
Num. arom. heavy atoms : 20
Fraction Csp3 : 0.33
Num. rotatable bonds : 8
Num. H-bond acceptors : 8.0
Num. H-bond donors : 1.0
Molar Refractivity : 148.34
TPSA : 104.86 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : Yes
CYP1A2 inhibitor : No
CYP2C19 inhibitor : Yes
CYP2C9 inhibitor : Yes
CYP2D6 inhibitor : Yes
CYP3A4 inhibitor : Yes
Log Kp (skin permeation) : -6.26 cm/s

Lipophilicity

Log Po/w (iLOGP) : 4.1
Log Po/w (XLOGP3) : 4.72
Log Po/w (WLOGP) : 5.01
Log Po/w (MLOGP) : 3.08
Log Po/w (SILICOS-IT) : 4.95
Consensus Log Po/w : 4.37

Druglikeness

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

Water Solubility

Log S (ESOL) : -6.05
Solubility : 0.00049 mg/ml ; 0.000000901 mol/l
Class : Poorly soluble
Log S (Ali) : -6.65
Solubility : 0.000121 mg/ml ; 0.000000223 mol/l
Class : Poorly soluble
Log S (SILICOS-IT) : -7.38
Solubility : 0.0000224 mg/ml ; 0.0000000412 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 3.0
Synthetic accessibility : 4.66

Safety of [ 929095-18-1 ]

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 [ 929095-18-1 ]

* 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 [ 929095-18-1 ]

[ 929095-18-1 ] Synthesis Path-Downstream   1~2

  • 2
  • [ 929095-51-2 ]
  • [ 929095-18-1 ]
YieldReaction ConditionsOperation in experiment
92% With ammonia In methanol at 80℃; for 40h; 3.1.F A mixture of methyl 5-{6-[(4-methylpiperazin-1-yl)methyl]-1H-benzimidazol-1- yl}-3-{(1 R)-1-[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxylate (15.82 g, 28.35 mmol) and 7N ammonia in MeOH (250 ml_, 1.75 mol) was added to a high-pressure glass reaction flask. The flask was sealed, then heated to 800C for approx. 40 h. The flask was cooled to room temperature, opened, and the reaction mixture concentrated under vacuum, then puriified by silica gel chromatography, eluting with a 2-to-8% gradient of MeOH/DCM with 1% ammonium hydroxide to give 14.11 g (92%) of the title compound as a white foam solid. 1H NMR (400 MHz, DMSO-Cf6): δ 8.49 (s, 1 H), 7.93 (d, 1H, J= 7.87 Hz), 7.86 (br s, 1 H), 7.80-7.75 (m, 2H), 7.68 (d, 1H, J= 8.23 Hz), 7.56 (t, 1 H, J= 7.68 Hz), 7.33 (s, 1H), 7.28 (d, 1 H, J- 8.42 Hz), 7.15 (br s, 1 H), 7.06 (s, 1 H), 5.94 (q, 1 H, J= 6.10 Hz), 3.52 (s, 2H), 2.45-2.20 (m, 8H), 2.13 (s, 3H), 1.74 (d, 3H, J= 6.22 Hz); MS (ESI): 544 [M+Hf .
92% With ammonia In methanol at 80℃; for 40h; 40.1.F; 40.3.F A mixture of methyl 5-{6-[(4-methylpiperazin-1-yl)methyl]-1 //-benzimidazol-1- yl}-3-{(1 R)A -[2-(trifluoromethyl)phenyl]ethoxy}thiophene-2-carboxylate (15.82 g, 28.35 mmol) and 7 N ammonia in methanol (250 ml_, 1.75 mol) was added to a high-pressure glass reaction flask. The flask was sealed, then heated to 80 0C for ~40 h. The flask was cooled to room temperature, opened, and the reaction mixture concentrated under vacuum, then puriified by silica gel chromatography, (2 to 8% methanokdichloromethane w/ 1% ammonium hydroxide) to give 14.11 g (92%) of the title compound as a white foam solid. 1H NMR (400 MHz, DMSO-ofe): δ 8.49 (s, 1 H), 7.93 (d, 1 H, J= 7.87 Hz), 7.86 (br s, 1 H)1 7.80-7.75 (m, 2H), 7.68 (d, 1 H1 J= 8.23 Hz)1 7.56 (t, 1 H1 J= 7.68 Hz)1 7.33 (s, 1 H)1 7.28 (d, 1 H, J= 8.42 Hz), 7.15 (br s, 1 H), 7.06 (s, 1 H), 5.94 (q, 1 H1 J= 6.10 Hz)1 3.52 (s, 2H)1 2.45-2.20 (m, 8H)1 2.13 (s, 3H)1 1.74 (d, 3H1 J= 6.22 Hz); MS (ESI): 544 [M+H]+.
89% With ammonia In methanol at 70℃; for 40 - 48h; Sealed tube;
60.2% With sodium methylate; formamide In tetrahydrofuran; methanol; toluene at 20 - 65℃; for 18h; Formamide (1.08mL, 26.5 mmol) followed by 25% w/w sodium methoxide in MeOH (1.82mL, 7.6mmol) are added to a solution of methyl 5-{6-[(4-methyl-1- piperazinyl)methyl]-1 /-/-benzimidazol-1-yl}-3-({(1R)-1-[2-(trifluoromethyl)phenyl]ethyl}oxy)-2-thiophenecarboxylate (5.Og, 8.95mmol) in THF (5OmL) and toluene (1 OmL) at room temperature. The reaction mixture is heated at ca 65 0C for about 18h and then cooled to ca 30 0C. The reaction mixture is diluted with EtOAc (25mL) and H2O (25mL) and then the biphasic mixture is separated. The organic phase is washed sequentially with H2O (25ml), saturated aqueous Na2C03and finally H2O (2 x 25mL). The organic phase is then concentrated by rotary evaporation and the concentrate diluted with EtOAc (3OmL) and then heated at ca 70 0C for about 1 h. The resulting suspension is then cooled to about 20 0C and stirred at this temperature for ca 18h. The suspension is then stirred at 0-5 0C for 2h and the product, isolated by filtration, washed with EtOAc (5ml_) and dried under vacuum at ca 25 0C to constant weight (2.93g, 60.2 %). δH (400 MHz, CDCI3) 1H NMR (400 MHz, DMSOd6): δ 8.49 (s, 1 H), 7.93 (d, 1 H, J = 7.87 Hz), 7.86 (br s, 1 H), 7.80-7.75 (m, 2H), 7.68 (d, 1 H, J = 8.23 Hz), 7.56 (t, 1 H, J = 7.68 Hz), 7.33 (s, 1 H), 7.28 (d, 1 H, J = 8.42 Hz), 7.15 (br s, 1 H), 7.06 (s, 1 H), 5.94 (q, 1 H, J = 6.10 Hz), 3.52 (s, 2H), 2.45-2.20 (m, 8H), 2.13 (s, 3H), 1.74 (d, 3H, J = 6.22 Hz); MS (ESI): 544 [M+H]+.

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