Compound based on benzimidazole substituted phenyl n-butylamide and preparation method of compound
A kind of technology of compound, mixture, be used in the compound based on phenyl n-butyramide substituted by benzimidazole and preparation field thereof
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Embodiment 1
[0191]The method of preparing intermediate IV is prepared from 3-methyl-4-n-butylamidobenzoic acid (V-1).
[0192]
[0193]1) Preparation of intermediate compound V-5
[0194]3-methyl-4-n-butylaminobenzoic acid (22.1 g, 100 mmol), triameter (10.4 g, 35 mmol, 0.35 eq) and tetrahydrofuran (70 ml) were added to 40 to 45 ° C, which were mixed to 40 to 45 ° C. Then N, N-dimethylformamide (365 mg, 5 mmol, 0.05 eq) was heated for 40 to 45 ° C for 5 to 6 hours, and then transferred to a constant voltage funnel after cooling. Another three-bottle was added to the addition of phytine (11.9 g, 110 mmol, 1.1 eq), acetonitrile (95 mL) and aqueous sodium hydroxide (8 g, 200 mmol, 2 eq in 200ml water), stirred under an ice bath at 0 ~ 5 ° C. Uniform. The prepared anchlor chloride was slowly added dropwise from the constant pressure funnel at 0 ~ 5 ° C to the reaction, and the drip was added to room temperature after 1 hour. The reaction was heated to remove an organic solvent of about half of the volume, a...
Embodiment 2
[0204]The method of preparing intermediate compound Vi-1 is prepared from the intermediate compound V-8.
[0205]
[0206]Compound V-8 (10 g, 55.2 mmol) is illegulated in dried 50 mL acetonitrile, DMF (400 mg, 5.5 mmol), three-yield (6.5 g, 22 mmol), N2Protection, acetonitrile reflux 2H, soluned, TLC showed the feedstock reaction. In another round of foil, nitrobenzamine (8.4 g, 55.2 mmol) is dissolved in 50 ml of dried acetonitrile, potassium carbonate (22.9 g, 165.6 mmol), an ice bath, and the acid chloride reaction droplets is added to the o-nitro. In the reaction solution of benzamine 2, N2Protection, acetonitrile refluxing 2H, concentrated reaction liquid, residual liquid plus 150 ml of water, 150 ml EA extraction, organic phase saturated sodium chloride washing, drying, cycles, column chromatography, gave compound Vi-1, pale yellow solid 14.5g, received Rate 83.3%.
[0207]Compound VI-1 characterization data:
[0208]1H NMR (400MHz, MeOD): 7.92 (DD, J = 8.3, 1.5 Hz, 1H), 7.64-7.76 (m, 3H)...
Embodiment 3
[0211]
[0212]1) Preparation of Compound V-12:
[0213]Compound V-8 (5 g, 27.6 mmol) was added to 25 mL of acetonitrile, and DMF (200 mg, 2.76 mmol) was added sequentially, and three photomics (3.27 g, 11.0 mmol), N2Protecting, acetonitrile refluxing 2 h, another round of methanol solution, add additional chloride solution under an ice bath, and 100 ml of EA, organic saturated saline was washed twice, dried, carried, to obtain Compound V-12, Yellow solid 5 g, yield 93.3%. Compound V-12 characterization data:
[0214]1H NMR (400MHz, CDCL3: Δ7.94 (DD, J = 8.4, 1.7 Hz, 1H), 7.75 (D, J = 1.9 Hz, 1H), 7.67 (DD, J = 8.4, 1.9 Hz, 1H), 6.62 (s, 1h) 3.00 (D, J = 4.8 Hz, 3H), 2.59 (S, 3H).
[0215]LR-MS (ESI) M / Z: 195.4 (M + H)+.
[0216]2) Preparation of Compound Vi-1
[0217]Compound V-12 (388 mg, 2 mmol), orthoxonitrobenzene (347 mg, 2.2 mmol), Pd (DPPF) Cl2(73mg, 0.1mmol), CS2CO3(1.95g, 6mmol) Add 10 mL of toluene, N2Protecting, 10 hours of heating, filtration, 20 mlea was diluted, and the organic phase...
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