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Dicyclohexylcarbodiimide → 8-[4-(6-Chloro-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-ylcarbonyl]-3,6,7,8-tetrahydrocyclopent[e]indole

HRID 275711
노트
인쇄 미리보기

반응식

HRID 275711 반응식
[CH:1]1[C:9]2[C:8]3[CH:10]([C:13]([OH:15])=O)[CH2:11][CH2:12][C:7]=3[CH:6]=[CH:5][C:4]=2[NH:3][CH:2]=1.[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]3[CH2:27][CH2:28][NH:29][CH2:30][CH:31]=3)=[CH:22][NH:23]2)=[CH:19][CH:18]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C1C=CN=CC=1.C1COCC1>[Cl:16][C:17]1[CH:25]=[C:24]2[C:20]([C:21]([C:26]3[CH2:27][CH2:28][N:29]([C:13]([CH:10]4[C:8]5[C:9]6[CH:1]=[CH:2][NH:3][C:4]=6[CH:5]=[CH:6][C:7]=5[CH2:12][CH2:11]4)=[O:15])[CH2:30][CH:31]=3)=[CH:22][NH:23]2)=[CH:19][CH:18]=1
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참가 물질

6

반응물 3

HCID 10868DicyclohexylcarbodiimideHCID 100598546-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1H-indoleHCID 185458923,6,7,8-Tetrahydrocyclopent[e]indole-8-carboxylic acid

생성물 1

HCID 185457998-[4-(6-Chloro-1H-indol-3-yl)-1,2,3,6-tetrahydropyridin-1-ylcarbonyl]-3,6,7,8-tetrahydrocyclopent[e]indole수율 38.5%

시약·촉매·용매 2

HCID 14284
4-(Dimethylamino)pyridine
촉매
HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 14a (1.4 g), 6-chloro-3-(1,2,3,6-tetrahydropyridin-4-yl)-1-H-indole (1.6 g), dicyclohexylcarbodiimid (1.9 g), and 4-dimethylaminopyridine (0.1 g) in THF (100 ml) was stirred for 24 hours at room temperature. The mixture was filtered and evaporated in vacuo. The residue was purified on silica gel eluted with ethyl acetate-heptane (3:2) giving 1.1 g of the title product as an amorpheous powder.

후처리

  1. filtrationThe mixture was filtered
  2. customevaporated in vacuo
  3. customThe residue was purified on silica gel
  4. washeluted with ethyl acetate-heptane (3:2)

출처 및 근거

ORD 기록
ord-d105dae424614a72a1a025e90ba688de
출처 데이터셋
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06352988B2

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