Diisopropylethylamine → Trifluoroacetic acid

HRID 521241Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 521241
[F:1][C:2]([F:8])([F:7])[CH2:3][C:4](O)=[O:5].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[F:33][C:34]([F:39])([F:38])[C:35]([O-:37])=[O:36].[C:40]([C:43]1[C:44]([NH:57][C:58]2[CH:63]=[CH:62][C:61]([F:64])=[CH:60][CH:59]=2)=[N:45][N:46]([C:48]2([CH2:54][C:55]#[N:56])[CH2:53][CH2:52][NH2+:51][CH2:50][CH2:49]2)[CH:47]=1)(=[O:42])[NH2:41].CCN(C(C)C)C(C)C>CN(C=O)C>[C:35]([OH:37])([C:34]([F:39])([F:38])[F:33])=[O:36].[C:55]([CH2:54][C:48]1([N:46]2[CH:47]=[C:43]([C:40]([NH2:41])=[O:42])[C:44]([NH:57][C:58]3[CH:59]=[CH:60][C:61]([F:64])=[CH:62][CH:63]=3)=[N:45]2)[CH2:53][CH2:52][N:51]([C:4](=[O:5])[CH2:3][C:2]([F:8])([F:7])[F:1])[CH2:50][CH2:49]1)#[N:56]

Komponenten

7

Edukt 4

HCID 81531DiisopropylethylamineHCID 27779723,3,3-Trifluoropropionic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 867294014-(4-carbamoyl-3-((4-fluorophenyl)amino)-1H-pyrazol-1-yl)-4-(cyanomethyl)piperidin-1-ium 2,2,2-trifluoroacetate2×

Produkt 2

HCID 6422Trifluoroacetic acidHCID 867294171-(4-(Cyanomethyl)-1-(3,3,3-trifluoropropanoyl)piperidin-4-yl)-3-(4-fluorophenylamino)-1H-pyrazole-4-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

3,3,3-Trifluoropropanoic acid (0.009 mL, 0.1 mmol) and HATU (40 mg, 0.11 mmol) were combined in DMF (0.15 mL) and allowed to stir at ambient temperature for 5 minutes. A solution of 4-{4-carbamoyl-3-[(4-fluorophenyl)amino]-1H-pyrazol-1-yl}-4-(cyanomethyl)piperidinium trifluoroacetate (Intermediate #38-5) (30 mg, 0.066 mmol) in DMF (0.10 mL) was then added to the reaction mixture, followed by DIPEA (0.045 mL, 0.26 mmol). The resulting solution was allowed to stir at ambient temperature for 16 hours. The mixture was then purified directly by mass-triggered reverse-phase preparative HPLC (MeCN/water, with 0.1% v/v TFA modifier) to afford the title compound, Example #35-1.

Aufarbeitung

  1. stirringto stir at ambient temperature for 16 hours
  2. customThe mixture was then purified directly by mass-triggered reverse-phase preparative HPLC (MeCN/water

Quellen und Nachweise

ORD-Eintrag
ord-06c61c675a614ba2bd1d517aad6a3682
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09328099B2

Notizen zur Reaktion

Wird geladen…