Diisopropylethylamine → Benzimidazole

HRID 900058

反応式

HRID 900058 の反応式
C1NC2N([C@@H]3O[C@H](CO)[C@@H](O)[C@H]3O)C=NC=2C(=S)N=1.[N:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[NH:22][CH:21]=1.CO.[I-].C(C[P+](C)(C)C)#N.C(N(C(C)C)CC)(C)C>C(#N)CC.O>[N:20]1[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=2[NH:22][CH:21]=1

参加物

7

反応物 4

HCID 81531DiisopropylethylamineHCID 6761666-ThioinosineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 23299442HCID 23299442、化合物

生成物 1

HCID 5798Benzimidazole

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 7854Propionitrile溶媒

実験手順

Benzimidazole analogs were synthesized by a Mitsunobu coupling (Zaragoza, F. Tetrahedron 2001, 57, 5451-5454 and Zaragoza, F.; Stephensen, H. J. Org. Chem. 2001, 66, 2518-2521) of 6-mercaptopurine riboside with benzimidazole-methyl alcohol (Kimura, T.; Takase, Y.; Hayashi, K.; Tanaka, H.; Ohtsuka, I.; Saeki, T.; Kogushi, M.; Yamada, T.; Fujimori, T.; Saitou, I.; Akasaka, K. J. Med. Chem. 1993, 36, 1630-1640), in the presence of (cyanomethyl)trimethylphosphonium iodide (36) and diisopropylethylamine (DIPEA) in propionitrile (Scheme 4). After refluxing of this mixture for 18 hr, water was added and the product precipitated. The direct use of alcohol 34 and 35 is an advantage of this method compared to the previous reactions. (Temple, C.; Kussner, C. L.; Montgomery, J. A. J. Org. Chem. 1968, 11, 41-43). These alcohols were prepared from reduction of the appropriate esters via standard procedures. (Sun, Q.; Gatto, B.; Yu, C.; Liu, A.; Liu, L. F.; LaVoie, E. J. J. Med. Chem. 1995, 38, 3638-3644).

後処理

  1. temperatureAfter refluxing of this mixture for 18 hr
  2. customthe product precipitated

出典と根拠

ORDレコード
ord-d84d97087def468da7fdf9b39d5854c5
出典データセット
uspto-grants-2008_04
特許番号
US07358235B2

関連ノート

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