CAS: 160982-10-5; 3-Acetyl-5-Chlorothiophene-2-Sulfonamide

相似化合物

160982-11-6 154127-28-3 138891-01-7

上下游产品

3-Acetyl-5-Chloro-2-Thiophenesulfenamide
3-乙酰基-5-氯噻吩-2-磺酰氯 3-Acetyl-5-Chloro-2-Thiophenesulfonyl Chloride 165117-07-7
3-Acetyl-5-Chloro-2-Thiophenesulfenyl Chloride

1-(2-(苄基硫代)-5-氯噻吩-3-基)乙酮置于sodium Tungstate (Vi) Dihydrate,氨,双氧水,氯体系中,用 水,甲苯 用作溶剂,化学反应 20.42H,反应生成3-乙酰基-5-氯噻吩-2-磺酰胺
参考文献:Enantioselective Synthesis Of Brinzolamide (Al-4862),A New Topical Carbonic Anhydrase Inhibitor. The "dcat Route" To Thiophenesulfonamides
标题:Enantioselective Synthesis Of Brinzolamide (Al-4862),A New Topical Carbonic Anhydrase Inhibitor. The "dcat Route" To Thiophenesulfonamides
摘要:A Large Scale Synthesis Of The Topical Carbonic Anhydrase Inhibitors Al-4623A (13A . Hcl) And Al-4862 (13B) From 3-Acetyl-2,5-Dichlorothiophene ("Dcat",1) Is Described,Reaction Of 1 With Nasbn Gave Thioether 2,Which Was Converted Via Sulfenyl Chloride 3 And Sulfenamide 5 To Sulfonamide 6,Bromination Of 6 Gave Bromo Ketone 7,Which Upon Reduction With (+)-B-Chlorodiisopinocampheylborane And Cyclization Of The Resulting Bromohydrin Produced S Thieno[3,2-E]-1,2-Thiazine 8A (96% Ee) After Chromatography,Treatment Of 8A In Thf With N-Buli At-70 Degrees C Resulted In Li-Cl Exchange,Reaction Of The Thienyllithium With So2 And Hydroxylamine O-Sulfonic Acid Afforded Bis-Sulfonamide 11A,Protection Of 11A As The Acetinidate 12A,Followed By Tosylation And Amination,Gave R Amine 13A,The Synthesis Of 13B Proceeded Via Primary Sulfonamide 16,Which Was Brominated,Reduced,And Cyclized To Give S Thieno[3,2-E]-1,2-Thiazine 18 (>98% Ee). By Virtue Of The Ionizable Nh,18 Was Separable From Reduction Byproducts By Base Extraction. Alkylation Of 18 With 3-Bromopropyl Methyl Ether Afforded 8B,Which Was Converted As Above,Via 11B,To Al-4862 (13B),These Procedures Provided Multihundred Gram Lots Of 13A And 13B.
Doi:10.1021/op9802125

专利信息

专利号:US-8344136-B2
优先权日:2008-06-16
标题:Process for the preparation of brinzolamide
发明人：FALCHI ALESSANDRO; DE LUCCHI OTTORINO; CASTELLIN ANDREA
权利人:PHF S A; FALCHI ALESSANDRO; DE LUCCHI OTTORINO; CASTELLIN ANDREA
摘要:The present invention relates to a process for the preparation of Brinzolamide, or 2H-thieno[3,2-e]-1,2-thiazin-6-sulfonamide, 4-(ethyl amino)-3,4-dihydro-2-(3-methoxypropyl)-, 1,1-dioxide, (4R)-via intermediates 2,3-dihydro-4H-thieno[3,2-e]-1,2-thiazin-4-ones, 1,1-dioxide. Further objects of the present invention are the intermediates mentioned above and other intermediates of the synthesis.