Diisopropylethylamine → 4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-3-methoxy-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

HRID 1262111

Reaktionsgleichung

Reaktionsgleichung von HRID 1262111
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([C:15]2[N:23]3[C:18]([CH:19]=[N:20][C:21](O)=[N:22]3)=[CH:17][CH:16]=2)[CH:10]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)C(C)C)(C)C.[N-](S(C(F)(F)F)(=O)=O)S(C(F)(F)F)(=O)=O.[C:49]([O:53][C:54]([N:56]1[CH2:61][CH2:60][CH:59]([C:62]2[CH:67]=[CH:66][C:65]([NH2:68])=[C:64]([O:69][CH3:70])[CH:63]=2)[CH2:58][CH2:57]1)=[O:55])([CH3:52])([CH3:51])[CH3:50]>CN(C=O)C>[C:49]([O:53][C:54]([N:56]1[CH2:57][CH2:58][CH:59]([C:62]2[CH:67]=[CH:66][C:65]([NH:68][C:21]3[N:20]=[CH:19][C:18]4=[CH:17][CH:16]=[C:15]([C:11]5[CH:12]=[CH:13][CH:14]=[C:9]([S:6](=[O:7])(=[O:8])[NH:5][C:1]([CH3:2])([CH3:4])[CH3:3])[CH:10]=5)[N:23]4[N:22]=3)=[C:64]([O:69][CH3:70])[CH:63]=2)[CH2:60][CH2:61]1)=[O:55])([CH3:52])([CH3:51])[CH3:50]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 4176748N-Propyl-Methyl Piperidinium Bis(trifluoroMethylsulfonyl)ImideHCID 57416157Tert-butyl 4-(4-amino-3-methoxyphenyl)piperidine-1-carboxylateHCID 178449976HCID 178449976, Verbindung

Produkt 1

HCID 667120084-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-3-methoxy-phenyl}-piperidine-1-carboxylic acid tert-butyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

In a 10 mL sealed tube, to N-tert-Butyl-3-(2-hydroxy-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-benzenesulfonamide (120 mg, 0.3464 mmol) and N,N-Diisopropylethylamine (0.242 mL, 1.39 mmol) in 3.0 mL of anhydrous DMF was added N-Phenylbis(trifluoromethane-sulfonimide (136 mg, 0.381 mmol). After stirring at room temperature for 30 minutes, 4-(4-Amino-3-methoxy-phenyl)-piperidine-1-carboxylic acid tert-butyl ester (140 mg, 0.460 mmol) was added. The reaction mixture was heated at 65° C. for 2.5 days. The reaction mixture was purified via silica gel column chromatography using 100:1 DCM:MeOH as the eluant. The collected fractions afforded impure 4-{4-[7-(3-tert-Butylsulfamoyl-phenyl)-pyrrolo[2,1-f][1,2,4]triazin-2-ylamino]-3-methoxy-phenyl}-piperidine-1-carboxylic acid tert-butyl ester as a sticky brown solid.

Aufarbeitung

  1. customIn a 10 mL sealed tube
  2. temperatureThe reaction mixture was heated at 65° C. for 2.5 days
  3. customThe reaction mixture was purified via silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-c00a0809f58a48fb81cc5b8d8b7d9c38
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08471005B2

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