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[ CAS No. 1372540-25-4 ] {[proInfo.proName]}

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Chemical Structure| 1372540-25-4
Chemical Structure| 1372540-25-4
Structure of 1372540-25-4 * Storage: {[proInfo.prStorage]}
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Product Details of [ 1372540-25-4 ]

CAS No. :1372540-25-4 MDL No. :MFCD22417098
Formula : C22H22F3N3O3 Boiling Point : -
Linear Structure Formula :- InChI Key :XTKLTGBKIDQGQL-UHFFFAOYSA-N
M.W : 433.42 Pubchem ID :56949517
Synonyms :

Calculated chemistry of [ 1372540-25-4 ]

Physicochemical Properties

Num. heavy atoms : 31
Num. arom. heavy atoms : 15
Fraction Csp3 : 0.36
Num. rotatable bonds : 5
Num. H-bond acceptors : 7.0
Num. H-bond donors : 1.0
Molar Refractivity : 113.1
TPSA : 67.59 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 : No
Log Kp (skin permeation) : -6.13 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.96
Log Po/w (XLOGP3) : 3.96
Log Po/w (WLOGP) : 5.03
Log Po/w (MLOGP) : 3.18
Log Po/w (SILICOS-IT) : 4.25
Consensus Log Po/w : 3.87

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.85

Water Solubility

Log S (ESOL) : -5.05
Solubility : 0.00386 mg/ml ; 0.00000891 mol/l
Class : Moderately soluble
Log S (Ali) : -5.08
Solubility : 0.00361 mg/ml ; 0.00000832 mol/l
Class : Moderately soluble
Log S (SILICOS-IT) : -6.12
Solubility : 0.000329 mg/ml ; 0.000000759 mol/l
Class : Poorly soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.12

Safety of [ 1372540-25-4 ]

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 [ 1372540-25-4 ]

* 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.

  • Upstream synthesis route of [ 1372540-25-4 ]
  • Downstream synthetic route of [ 1372540-25-4 ]

[ 1372540-25-4 ] Synthesis Path-Upstream   1~6

  • 1
  • [ 1372540-24-3 ]
  • [ 1372540-25-4 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: With water; lithium hydroxide In tetrahydrofuran at 50℃; for 1 h;
Stage #2: Acidic conditions
An aqueous solution of 2 N LiOH (1.2 mL) was added to a solution of methyl 2-methyl-1-[2-methyl-3-(trifluoromethyl)phenyl]methyl}-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylate, prepared as described in Example 30 (180 mg, 0.4 mmol) in THF (10 mL) and stirred at 50° C. for 1 h.
When TLC showed no starting material remaining, the mixture was cooled to rt and THF was removed under reduced pressure.
The pH of the mixture was acidified to pH 3.
The suspension was filtered and the filtrate was collected, and washed with water (10 mL) to give the product as a white solid (152 mg, yield 88percent).
1H NMR (300 MHz, DMSO-d6): δ ppm 2.46 (s, 3H), 2.54 (s, 3H), 3.10 (t, 4H, J=4.8 Hz), 3.73 (t, 4H, J=4.8 Hz), 5.63 (s, 2H), 6.37 (d, 1H, J=7.8 Hz), 7.26 (t, 1H, J=7.8 Hz), 7.35 (d, 1H, J=2.4 Hz), 7.44 (d, 1H, J=2.4 Hz), 7.62 (d, 1H, J=7.8 Hz); LC-MS: m/e=434 [M+1]+.
88% With water; lithium hydroxide In tetrahydrofuran at 50℃; for 1 h; An aqueous solution of 2 N LiOH (1.2 mL) was added to a solution of methyl 2-methyl-1-[2-methyl-3-(trifluoromethyl)phenyl]methyl}-6-(4-morpholinyl)-1H-benzimidazole-4-carboxylate, prepared as described above, (180 mg, 0.4 mmol) in THF (10 mL) and stirred at 50° C. for 1 h.
When TLC showed no starting material remaining, the mixture was cooled to rt and THF was removed under reduced pressure.
The pH of the mixture was acidified to pH 3.
The suspension was filtered and the filtrate was collected, and washed with water (10 mL) to give the product as a white solid (152 mg, yield 88percent).
1H NMR (300 MHz, DMSO-d6): δ ppm 2.46 (s, 3H), 2.54 (s, 3H), 3.10 (t, 4H, J=4.8 Hz), 3.73 (t, 4H, J=4.8 Hz), 5.63 (s, 2H), 6.37 (d, 1H, J=7.8 Hz), 7.26 (t, 1H, J=7.8 Hz), 7.35 (d, 1H, J=2.4 Hz), 7.44 (d, 1H, J=2.4 Hz), 7.62 (d, 1H, J=7.8 Hz); LC-MS: m/e=434 [M+1]+.
152 mg With water; lithium hydroxide In tetrahydrofuran at 50℃; for 1 h; An aqueous solution of 2 N LiOH (1.2 mL) was added to a solution of methyl 2-methyl- 1 - { [2-methyl-3-(trifluoromethyl)phenyl]methyl} -6-(4-morpholinyl)- 1 H-benzimidazole- 4-carboxylate, prepared as described above, (180 mg, 0.4 mmol) in THF (10 mL) and stirred at 50° C for 1 h. When TLC showed no starting material remaining, the mixture was cooled to rt and THF was removed under reduced pressure. The pH of the mixture was acidified to pH 3. The suspension was filtered and the filtrate was collected, and washed with water (lOmL) to give the product as a white solid (152 mg, yield 88percent). FontWeight="Bold" FontSize="10" H NMR (300 MHz, DMSO-de): δ ppm 2.46 (s, 3H), 2.54 (s, 3H), 3.10 (t, 4H, J=4.8 Hz), 3.73 (t, 4H, J=4.8 Hz), 5.63 (s, 2H), 6.37 (d, IH, J=7.8 Hz), 7.26 (t, IH, J=7.8 Hz), 7.35 (d, IH, J=2.4 Hz), 7.44 (d, IH, J=2.4 Hz), 7.62 (d, IH, J=7.8 Hz); LC-MS: m/e = 434 [M+l]+ .
Reference: [1] Patent: US2012/88767, 2012, A1, . Location in patent: Page/Page column 35
[2] Patent: US2016/287610, 2016, A1, . Location in patent: Paragraph 0054; 0055
[3] Patent: WO2015/42029, 2015, A1, . Location in patent: Page/Page column 17
  • 2
  • [ 2516-95-2 ]
  • [ 1372540-25-4 ]
Reference: [1] Patent: US2012/88767, 2012, A1,
  • 3
  • [ 1203486-58-1 ]
  • [ 1372540-25-4 ]
Reference: [1] Patent: US2012/88767, 2012, A1,
[2] Patent: WO2015/42029, 2015, A1,
[3] Patent: US2016/287610, 2016, A1,
  • 4
  • [ 193481-78-6 ]
  • [ 1372540-25-4 ]
Reference: [1] Patent: US2012/88767, 2012, A1,
  • 5
  • [ 874301-23-2 ]
  • [ 1372540-25-4 ]
Reference: [1] Patent: US2012/88767, 2012, A1,
  • 6
  • [ 1372540-21-0 ]
  • [ 1372540-25-4 ]
Reference: [1] Patent: US2012/88767, 2012, A1,
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