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Process for the preparation of n-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfonamido-dibenzo[b,d]furan-1-carboxamide

A technology of difluoromethoxyl and dichloropyridine, applied in chemical instruments and methods, preparation of organic compounds, organic chemistry, etc.

Inactive Publication Date: 2007-11-21
GLENMARK PHARMACEUTICALS LIMITED
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0003] Although multiple research organizations around the world are working to discover highly selective PDE-4 isoenzyme inhibitors, only limited progress has been made so far

Method used

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  • Process for the preparation of n-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfonamido-dibenzo[b,d]furan-1-carboxamide
  • Process for the preparation of n-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfonamido-dibenzo[b,d]furan-1-carboxamide
  • Process for the preparation of n-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfonamido-dibenzo[b,d]furan-1-carboxamide

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0163] 4-Cyclopentyloxy-3-hydroxybenzaldehyde

[0164] Under stirring, in the temperature range of 25-35°C, add DMF (3.5L) 3,4-dihydroxybenzaldehyde (1.15Kg, 8.3 M), cyclopentyl bromide (3.1 kg, 20.3M) and powdered anhydrous potassium carbonate (1.15 kg, 20.3M). The reaction mixture was heated to 75-80° C. with stirring and stirring was continued for 1 hour. Powdered potassium carbonate (140 g, 1M) was added to the reaction mixture at 75-80°C with stirring. After the addition was complete, the reaction mixture was maintained at 75-80°C for 1 hour. The progress of the reaction was monitored by thin layer chromatography and HPLC. After confirming that the reaction was complete, the reaction mixture was cooled to 25-35°C and filtered. The inorganic salt filter cake was washed with DMF (300ml×2), and the washing liquid and the filtrate were combined. The organic layer was concentrated under high vacuum below 75 °C. Toluene (2 L) was added to the residue after distillation of...

Embodiment 2

[0166] 2-Bromo-1-fluoro-4-nitrobenzene

[0167] Under stirring, add DM water (550ml), concentrated sulfuric acid (6.2L, 113M), 4-fluoronitrobenzene (1.0 kg, 7.09M). The reaction mixture was cooled to 10°C and bromine (1.13 kg, 7.06M) was added to the reaction mixture with stirring. The reaction mixture was cooled to 25-35°C, silver sulfate (1.1 kg, ~3.53M) was added to the reaction mixture in one portion at 25-35°C and stirring was continued for 30-32 hours. The progress of the reaction was monitored by GC, and after completion of the reaction was determined, the reaction mixture was slowly poured into a mixture of ice-cold water (12 L) and dichloromethane (12 L). The insolubles were filtered and the inorganics were washed with dichloromethane (2 L). The combined organic layers were washed with 10% sodium bicarbonate (3 L), water (5 L). The dichloromethane layer was distilled in vacuo below 40°C, and n-hexane (4.5 L) was added to the residue. The resulting material was st...

Embodiment 3

[0169] 4-Cyclopentyloxy-3-(4'-nitro-2'-bromophenoxy)benzaldehyde

[0170] Under stirring, add dimethyl sulfoxide (4.5 L), 4-cyclopentyloxy-3-hydroxybenzaldehyde ( 900g, 4.36M), potassium fluoride (510g, 8.5M), 2-bromo-1-fluoro-4-nitrobenzene (970g, 4.38M). The reaction mixture was heated to 95-100°C and stirring was continued for 18-20 hours with stirring. The reaction mixture was cooled to 25-35°C, water (4.5 L) was added to the reaction mixture and stirring was continued for 2 hours. The precipitated product was filtered, washed with water (3L×3), 5% sodium hydroxide solution (2L×2), water (5L×4), and finally n-hexane (4.5L×2). The product was dried under vacuum. Oven temperature was 55-60°C until MC reached <1%. The dried product is light yellow solid, weighing 1.689kg-1.7kg, yield 70-77%, m.p 95-96°C, HPLC purity 97-98%, m.p.92-94°C. IR(KBr) spectrum showed 3150 (CH str), 2960 (CH str), 1682 (CHO str), 1340 (NO2 str). 1H-NMR (DMSO-d6) showed δ9.8(s, 1H), 8.8(s, 1H), ...

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Abstract

The present invention relates to a method of preparing N-(3,5-dichloropyrid-4-yl)-4-difluoromethoxy-8-methanesulfonamido-dibenzo[b,d]furan-1-carboxamide and pharmaeutically acceptable salts thereof, such as its sodium salt, and novel intermediate compounds useful in the synthesis of the aforementioned compound.

Description

[0001] This application claims U.S. Provisional Application No. 60 / 618,474, filed October 13, 2004, Indian Provisional Application No. 1099 / Mum / 2004, filed October 14, 2004, and U.S. Provisional Application No. 1099 / Mum / 2004, filed October 21, 2004. Priority of Application No. 60 / 621,981, both of which are hereby incorporated by reference. technical field [0002] The present invention relates to the preparation of N-(3,5-dichloropyridin-4-yl)-4-difluoromethoxy-8-methanesulfinamido-dibenzo[b,d]furan-1-methanol Processes for amides and pharmaceutically acceptable salts thereof (such as sodium salts thereof) and novel intermediate compounds employed in the synthesis of the aforementioned compounds. Background technique [0003] Although multiple research organizations around the world are working to discover highly selective PDE-4 isoenzyme inhibitors, only limited progress has been made so far. Many compounds are inhibitory to PDE-4. SmithKline Beecham's 'Ariflo', Byk Gulde...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C201/12C07D307/91C07C205/38
Inventor B·高普兰L·A·加拉特B·钱德拉塞卡拉B·G·皮莱
Owner GLENMARK PHARMACEUTICALS LIMITED
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