Triphenylphosphine → 4-[3-(4-Methylpiperazin-1-yl)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone

HRID 21127

Reaktionsgleichung

Reaktionsgleichung von HRID 21127
[OH:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]2[N:12]([C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])[C:13]3[C:18]([CH:19]=2)=[CH:17][C:16]([CH2:20][N:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[CH:15][CH:14]=3)=[C:7]2[C:3]=1[CH2:4][NH:5][C:6]2=[O:34].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.C1(C)C=CC=CC=1.O[CH2:74][CH2:75][CH2:76][N:77]1[CH2:82][CH2:81][N:80]([CH3:83])[CH2:79][CH2:78]1>C1COCC1>[CH3:83][N:80]1[CH2:81][CH2:82][N:77]([CH2:76][CH2:75][CH2:74][O:1][C:2]2[CH:10]=[CH:9][C:8]([C:11]3[N:12]([C:27]([O:29][C:30]([CH3:31])([CH3:33])[CH3:32])=[O:28])[C:13]4[C:18]([CH:19]=3)=[CH:17][C:16]([CH2:20][N:21]3[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]3)=[CH:15][CH:14]=4)=[C:7]3[C:3]=2[CH2:4][NH:5][C:6]3=[O:34])[CH2:78][CH2:79]1

Komponenten

6

Edukt 4

HCID 11776TriphenylphosphineHCID 792083-(4-Methyl-1-piperazine)propan-1-olHCID 684932224-Hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneHCID 87147022ethyl (NE)-N-ethoxycarbonyliminocarbamate;toluene

Produkt 1

HCID 684943904-[3-(4-Methylpiperazin-1-yl)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinoneAusbeute 58 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In a similar manner to Step 1 of Example 149, 4-hydroxy-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0817 g, 0.177 mmol) was dissolved in THF (4.0 mL), and the solution was treated with triphenylphosphine (0.0930 g, 0.354 mmol), 40% DEAD-toluene solution (0.161 mL, 0.354 mmol) and 1-(3-hydroxypropyl)-4-methylpiperazine (0.140 g, 0.855 mmol), followed by purification by flash column chromatography (chloroform/methanol=7/3) to obtain 4-[3-(4-methylpiperazin-1-yl)propoxy]-7-[1-(tert-butoxycarbonyl)-5-(piperidinomethyl)indol-2-yl]isoindolinone (0.0617 g, yield 58%).

Aufarbeitung

  1. customfollowed by purification by flash column chromatography (chloroform/methanol=7/3)

Quellen und Nachweise

ORD-Eintrag
ord-dd7ea8f8269541f4b6b7d776bb81b4de
Quelldatensatz
uspto-grants-2010_06
Patentnummer
US07745641B2

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