Trifluoroacetic acid → HCID 72948500, Verbindung

HRID 1430809Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1430809
[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH:15]3[CH2:18][C:17]([F:20])([F:19])[CH2:16]3)[CH2:10][CH2:9]2)=[CH:6][C:5]([C:21]#[N:22])=[CH:4][C:3]=1[NH:23][C:24]1[N:29]=[C:28]([N:30]([CH:40]2[CH2:42][CH2:41]2)CC2C=CC(OC)=CC=2)[C:27]2=[N:43][CH:44]=[C:45]([C:46]#[N:47])[N:26]2[N:25]=1.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>ClCCl>[Cl:1][C:2]1[C:7]([N:8]2[CH2:13][CH2:12][CH:11]([NH:14][CH:15]3[CH2:16][C:17]([F:20])([F:19])[CH2:18]3)[CH2:10][CH2:9]2)=[CH:6][C:5]([C:21]#[N:22])=[CH:4][C:3]=1[NH:23][C:24]1[N:29]=[C:28]([NH:30][CH:40]2[CH2:41][CH2:42]2)[C:27]2=[N:43][CH:44]=[C:45]([C:46]#[N:47])[N:26]2[N:25]=1

Komponenten

5

Edukt 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 867084932-((2-Chloro-5-cyano-3-(4-((3,3-difluorocyclobutyl)amino)piperidin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile

Produkt 1

HCID 72948500HCID 72948500, VerbindungAusbeute 11,9 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a round bottom flask charged with 2-((2-chloro-5-cyano-3-(4-((3,3-difluorocyclobutyl)amino)piperidin-1-yl)phenyl)amino)-4-(cyclopropyl(4-methoxybenzyl)amino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (34.9 mg, 0.053 mmol) in dichloromethane (530 μl) was added anisole (116 μl, 1.060 mmol), followed by the slow addition of trifluoroacetic acid (408 μl, 5.30 mmol). The reaction mixture was stirred at rt 2 d. Excess TFA was removed in vacuo. The crude residue was taken up in MeOH and free based using a Phenomenex Strata 1 g SCX column. The crude solid was purified via preparative LC/MS and provided 2-((2-chloro-5-cyano-3-(4-((3,3-difluorocyclobutyl)amino)piperidin-1-yl)phenyl)amino)-4-(cyclopropylamino)imidazo[2,1-f][1,2,4]triazine-7-carbonitrile (3.4 mg).

Aufarbeitung

  1. customExcess TFA was removed in vacuo
  2. customThe crude solid was purified via preparative LC/MS

Quellen und Nachweise

ORD-Eintrag
ord-3011f02b2c99469bab9fbdb9f1e387bb
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08940736B2

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