Diisopropylethylamine → Benzimidazole

HRID 900058

반응식

HRID 900058 반응식
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

참가 물질

7

반응물 4

HCID 81531DiisopropylethylamineHCID 6761666-ThioinosineHCID 10514344(Cyanomethyl)trimethylphosphanium iodideHCID 23299442HCID 23299442, 화합물

생성물 1

HCID 5798Benzimidazole

시약·촉매·용매 2

HCID 962Water용매HCID 7854Propionitrile용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-d84d97087def468da7fdf9b39d5854c5
출처 데이터셋
uspto-grants-2008_04
특허 번호
US07358235B2

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