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Chemical Structure| 1372540-21-0 Chemical Structure| 1372540-21-0

Structure of 1372540-21-0

Chemical Structure| 1372540-21-0

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Product Details of [ 1372540-21-0 ]

CAS No. :1372540-21-0
Formula : C14H17N3O3
M.W : 275.31
SMILES Code : O=C(C1=C2N=C(C)NC2=CC(N3CCOCC3)=C1)OC

Safety of [ 1372540-21-0 ]

Application In Synthesis of [ 1372540-21-0 ]

* 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 [ 1372540-21-0 ]

[ 1372540-21-0 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 1372540-21-0 ]
  • [ 81093-21-2 ]
  • C23H27N3O3 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h; To a solution of methyl 2-methyl-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate, prepared as described in Example 26, step d (0.2 g, 0.726 mmol) in N,N-Dimethylformamide (DMF) (10 mL) was added <strong>[81093-21-2]2,3-dimethylbenzyl bromide</strong> (0.289 g, 1.453 mmol) and potassium carbonate (0.301 g, 2.179 mmol), The resulting reaction mixture was stirred for 3 h at 80 C. The solution was cooled to room temperature and poured into water and was extracted with EtOAc. The combined organic phase was washed with Brine and concentrated. The residue was purified on Biotage Isolera purification system using a Biotage 10 g SNAP silica gel cartridge and eluted with a gradient of DCM to 5% MeOH/DCM over 10 column volumes. The expected compound was collected and evaporated to yield a tan solid. The tan solid was dissolved in tetrahydrofuran (THF) (10.00 mL) followed by the addition of 1M lithium hydroxide solution (10 mL, 10 mmol). The reaction was stirred at 50 C. for 2 h. The reaction was cooled to room temperature and the organic solvent was removed in vacuo. The solution was diluted with water (20 mL) and acidified with 1 N HCl. The mixture was then filtered and the grey solid was purified by reversed phase HPLC with a gradient of acetonitrile (0.1% TFA) and water (0.1% TFA v/v) (20-50%) over 10 minutes. The appropriate fractions were collected and evaporated to yield the desired product (55.2 mg, 0.145 mmol, 20.02% yield). 1H NMR (400 MHz, CHLOROFORM-d) delta ppm 2.31 (s, 3H) 2.36 (s, 3H) 2.85 (s, 3H) 3.13-3.24 (m, 4H) 3.80-3.96 (m, 4H) 5.49-5.61 (m, 2H) 6.29-6.38 (m, 1H) 6.94-6.99 (m, 1H) 7.00-7.07 (m, 1H) 7.14-7.23 (m, 1H) 7.72 (m, 1H). MS(ES+) m/e 379.8 [M+H]+.
  • 2
  • [ 261952-16-3 ]
  • [ 1372540-21-0 ]
  • [ 1372540-24-3 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In N,N-dimethyl-formamide; at 80℃; for 3h; A solution of methyl 2-methyl-5-(4-morpholinyl)-1H-benzimidazole-7-carboxylate prepared as described in Example 26, step d (500 mg, 1.8 mmol), <strong>[261952-16-3]1-(bromomethyl)-2-methyl-3-(trifluoromethyl)benzene</strong> (483 mg, 1.9 mmol) and K2CO3 (497 mg, 3.6 mmol) in DMF (50 mL) was stirred at 80 C. for 3 h. The reaction mixture was cooled to rt and poured into water (50 mL), extracted with EtOAc (30 mL*3). The combined organic layers were washed with brine, dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel chromatography eluted with DCM:MeOH=50:1 to give the crude product (230 mg, yield 29%), as a white solid. 1H NMR (300 MHz, DMSO-d6): δ ppm 2.39 (s, 3H), 2.54 (s, 3H), 3.08 (t, 4H, J=4.8 Hz), 3.72 (t, 4H, J=4.8 Hz), 3.89 (s, 3H), 5.57 (s, 2H), 6.27 (d, 1H, J=7.5 Hz), 7.22 (t, 1H, J=7.5 Hz), 7.27 (d, 1H, J=2.4 Hz), 7.38 (d, 1H, J=2.4 Hz) 7.60 (d, 1H, J=7.5 Hz); LC-MS: m/e=448 [M+1]+
 

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