Phthalimide → 2-(1-{5-[5-(4-isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethyl)-1H-isoindole-1,3(2H)-dione

HRID 404891노트

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HRID 404891 반응식
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:14][C:13]([C:15]3[S:19][C:18]([CH:20](O)[CH3:21])=[CH:17][CH:16]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].[C:25]1(=[O:35])[NH:29][C:28](=[O:30])[C:27]2=[CH:31][CH:32]=[CH:33][CH:34]=[C:26]12.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>O1CCCC1>[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:14][C:13]([C:15]3[S:19][C:18]([CH:20]([N:29]4[C:25](=[O:35])[C:26]5[C:27](=[CH:31][CH:32]=[CH:33][CH:34]=5)[C:28]4=[O:30])[CH3:21])=[CH:17][CH:16]=3)=[N:12][N:11]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2]

참가 물질

6

반응물 4

HCID 6809PhthalimideHCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 694341721-{5-[5-(4-Isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethanol

생성물 1

HCID 694368152-(1-{5-[5-(4-isopropoxyphenoxy)-1,3,4-thiadiazol-2-yl]thien-2-yl}ethyl)-1H-isoindole-1,3(2H)-dione수율 277.8%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
25 °C

실험 절차

A solution of Example 24E (0.37 g, 1.025 mmol), phthalimide (0.151 g, 1.025 mmol), and triphenyl phosphine (0.537 g, 2.05 mmol) in tetrahydrofuran (5 mL) was treated with diisopropyl azodicarboxylate (0.385 mL, 1.85 mmol) and the resulting solution was stirred at 25° C. for 3 hours. The reaction was concentrated under reduced pressure on a rotary evaporator to provide 1.4 g of a yellow oil. The concentrate was purified by flash chromatography on silica gel eluting with a solvent gradient from 1% to 20% ethyl acetate in hexanes to provide 0.49 g (98%) of the title compound as a white solid. 1H NMR (300 MHz, DMSO-d6) δ ppm 7.76-7.98 (m, 4H) 7.51 (d, J=3.68 Hz, 1H) 7.38 (d, J=9.19 Hz, 2H) 7.14 (dd, J=3.68, 0.92 Hz, 1H) 7.01 (d, J=9.19 Hz, 2H) 5.60-5.77 (m, 1H) 4.55-4.70 (m, 1H) 1.88 (d, J=7.35 Hz, 3H) 1.27 (d, J=5.88 Hz, 6H); MS (ESI) m/z 492 (M+H)+.

후처리

  1. concentrationThe reaction was concentrated under reduced pressure on a rotary evaporator

출처 및 근거

ORD 기록
ord-15fb4ba0bf234db593ac608364e8be38
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748627B2

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