N-(6-(7-amino-4-methoxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)naphthalen-2-yl)methanesulfonamide hydrochloride | 1597548-54-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-(6-(7-amino-4-methoxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)naphthalen-2-yl)methanesulfonamide hydrochloride
• CAS: 1597548-54-3
• 化学式: C₂₂H₂₄N₂O₄S*ClH
• 分子量: 448.971
• InChiKey: WYWCZFCQCRWVJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.56
• 重原子数：
  30.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  90.65
• 氢给体数：
  2.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  N-(6-(7-amino-4-methoxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)naphthalen-2-yl)methanesulfonamide hydrochloride 以 甲醇 、 水 为溶剂， 以100%的产率得到N-(6-(7-amino-4-methoxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)naphthalen-2-yl)methanesulfonamide
  参考文献：
  名称：

  A Scalable Route to an Unusual 3,3-Dimethyl-2,3-dihydrobenzofuran Ring System Present in an HCV Drug Candidate

  摘要：

  A scalable synthesis of a key intermediate used for the preparation of an HCV inhibitor containing an unusual dimethyldihydrobenzofuran ring is described. A key element for the successful completion of the synthesis was the correct ordering of a sequence of bromination, chlorination, and methylation to provide optimized selectivity and improved yield. A tin hydride-mediated ring closure was replaced with a more environmentally benign sulfuric acid-catalyzed Friedel-Crafts reaction. The overall yield for the preparation of the key intermediate was increased from less than 5 to 40%.

  DOI：

  10.1021/op4003467
• 作为产物：
  描述：

  N-(6-溴萘-2-基)甲烷磺酰胺 在 盐酸 、 potassium phosphate 、 palladium diacetate 、 2-二环己基磷-2,4,6-三异丙基联苯 、 三环己基膦 作用下， 以 1,4-二氧六环 、 水 、 乙酸乙酯 、 N,N-二甲基甲酰胺 为溶剂， 反应 8.5h， 生成 N-(6-(7-amino-4-methoxy-3,3-dimethyl-2,3-dihydrobenzofuran-5-yl)naphthalen-2-yl)methanesulfonamide hydrochloride
  参考文献：
  名称：

  A Scalable Route to an Unusual 3,3-Dimethyl-2,3-dihydrobenzofuran Ring System Present in an HCV Drug Candidate

  摘要：

  A scalable synthesis of a key intermediate used for the preparation of an HCV inhibitor containing an unusual dimethyldihydrobenzofuran ring is described. A key element for the successful completion of the synthesis was the correct ordering of a sequence of bromination, chlorination, and methylation to provide optimized selectivity and improved yield. A tin hydride-mediated ring closure was replaced with a more environmentally benign sulfuric acid-catalyzed Friedel-Crafts reaction. The overall yield for the preparation of the key intermediate was increased from less than 5 to 40%.

  DOI：

  10.1021/op4003467