Triethylamine → 4-Trifluoromethanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone

HRID 21220

반응식

HRID 21220 반응식
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][N:24]([CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:35])[CH3:34])([CH3:32])[CH3:31])[CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:44].C(N(CC)CC)C.[F:52][C:53]([F:59])([F:58])[S:54](Cl)(=[O:56])=[O:55]>ClCCl>[F:52][C:53]([F:59])([F:58])[S:54]([O:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:37]([O:39][C:40]([CH3:43])([CH3:42])[CH3:41])=[O:38])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:22][CH2:23][N:24]([CH2:27][CH2:28][O:29][Si:30]([C:33]([CH3:36])([CH3:34])[CH3:35])([CH3:32])[CH3:31])[CH2:25][CH2:26]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:44])(=[O:56])=[O:55]

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 79000Trifluoromethanesulfonyl chlorideHCID 685336154-Hydroxy-7-(1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl)isoindolinone

생성물 1

HCID 874868584-Trifluoromethanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone수율 77%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

In a similar manner to Step 1 of Example 299, 4-hydroxy-7-(1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl)isoindolinone (150 mg, 0.240-mmol) was suspended in dichloromethane (6.0 mL), and the suspension was treated with triethylamine (0.167 mL, 1.20 mmol) and trifluoromethanesulfonyl chloride (0.046 mL, 0.43 mmol) under ice-cooling, followed by purification by preparative thin-layer chromatography (chloroform/methanol=13/1) to obtain 4-trifluoromethanesulfonyloxy-7-{1-(tert-butoxycarbonyl)-5-[4-(2-tert-butyldimethylsilyloxyethyl)pyperazin-1-ylmethyl]indol-2-yl}isoindolinone (139 mg, yield 77%).

후처리

  1. temperaturecooling
  2. customfollowed by purification by preparative thin-layer chromatography (chloroform/methanol=13/1)

출처 및 근거

ORD 기록
ord-bd00f595929f45459f0139a881c76f6c
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07745641B2

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