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Telmisartan preparation method and intermediate of telmisartan
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A kind of technology of telmisartan and compound, applied in the field of preparation of intermediate
Inactive Publication Date: 2014-05-14
TOPHARMAN SHANGHAI +2
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[0009] The above synthetic methods are two-step, and there is still the possibility of further simplifying the process and reducing the cost
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Embodiment 1
[0104] Example 1: Preparation of 4'-chloromethylbiphenyl-2-carboxylic acid (II, R=COOH, X=Cl)
[0105] Add 4'-methylbiphenyl 2-carboxylic acid (IV) (10g, 0.047mol), azobisisobutylcyanide (AIBN) (0.11g, 1.5mol%) into chlorobenzene (35mL), stir, Heat to 90°C, slowly add SO 2 Cl 2 (3.8mL, 0.047mol) of chlorobenzene solution (15mL), after the dropwise addition, stir for 1 hour, and TLC detects that the reaction is over; the reaction solution is naturally cooled to room temperature, and solids are precipitated, then cooled in an ice bath for 1 hour, and suction filtered , the obtained filtrate was washed with toluene (10mL×2), and dried to obtain white granular solid II (9.5g, yield 82%). 1 H NMR (300MHz, DMSO-d6): 12.79 (s, 1H, OH), 7.21-7.75 (m, 8H, ArH), 4.81 (s, 2H, CH2), MS: 246.1.
Embodiment 2
[0106] Example 2: Preparation of 4'-chloromethylbiphenyl-2-carboxylic acid (II, R=COOH, X=Cl)
[0107] Add 4'-methylbiphenyl 2-carboxylic acid (IV) (10g, 0.047mol), azobisisobutylcyanide (AIBN) (0.11g, 1.5mol%) into chlorobenzene (70mL), stir, Heat to 80°C, add trichloroisocyanuric acid (10.9g, 0.047mol), stir for 12 hours, and filter out the insoluble matter; naturally cool the reaction solution to room temperature, and solids are precipitated, and the obtained filtrate is washed with toluene ( 10mL×2), dried to obtain white granular solid II (6g, yield 52%).
Embodiment 3
[0108] Example 3: Preparation of 4'-chloromethylbiphenyl-2-carboxylic acid (II, R=COOH, X=Cl)
[0109] Dissolve 4'-methylbiphenyl 2-carboxylic acid (IV) (10g, 0.047mol) in dichloromethane (150mL), add benzoyl peroxide (0.23g, 2mol%), add 1.1 equivalent of chlorine, The reaction was stirred for 12 hours; saturated aqueous sodiumbicarbonate solution was added to the reaction solution for extraction, the organic layer was separated, and the solvent was evaporated to dryness to obtain off-white solid II (6 g, yield 52%).
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Abstract
The invention relates to a telmisartan preparation method. The telmisartan preparation method is characterized in that 2-n-propyl-4-methyl-6-(1-methyl benzimidazole-2-yl) benzimidazole (compound I) and 4'-halomethyl diphenyl-2-substituted compound (compound II) carry out a nucleophilic substitution reaction to obtain a compound III; when R is COOH, the compound III is telmisartan; when R is COOR' or CN, the compound III is hydrolyzed to obtain the telmisartan.
Description
technical field [0001] The present invention relates to a preparation method of an antihypertensive drugTelmisartan (Telmisartan) and its intermediate, and also relates to a preparation method of these intermediates. Background technique [0002] Telmisartan is a new type of non-peptideangiotensin II (AT II) receptorantagonist, clinically used in the treatment of hypertension, its chemical name is 4'-[(1,4'-dimethyl-2 '-Propyl[2,6'-di-1H-benzimidazole]-1'-yl)methyl]-[1,1'-biphenyl]-2-carboxylic acid, the structure is as follows: [0003] [0004] The existing synthetic route of telmisartan mainly uses 3-methyl-4-aminobenzoic acid methyl ester as the starting material to obtain the intermediate through N-acylation, nitration, reduction, cyclization, ester hydrolysis, and condensation reactions. 2-n-propyl-4-methyl-6-(1-methylbenzimidazol-2-yl)benzimidazole (I), I and 4'-bromomethylbiphenyl-2-carboxylic acid tert-butyl The ester (V) undergoes a two-step reaction of nuc...
Claims
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