StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1) → N-{1-[4-(1-Cyano-1-methylethyl)phenyl]ethyl}-2-(7-fluoro-1H-benzimidazol-1-yl)acetamide

HRID 419981
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 419981
[F:1][C:2]1[C:7]2[N:8]([CH2:11][C:12]([OH:14])=O)[CH:9]=[N:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:16][CH:17]([C:19]1[CH:24]=[CH:23][C:22]([C:25]([CH3:29])([CH3:28])[C:26]#[N:27])=[CH:21][CH:20]=1)[CH3:18].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F>CN(C1C=CN=CC=1)C.CN(C=O)C>[C:26]([C:25]([C:22]1[CH:21]=[CH:20][C:19]([CH:17]([NH:16][C:12](=[O:14])[CH2:11][N:8]2[C:7]3[C:2]([F:1])=[CH:3][CH:4]=[CH:5][C:6]=3[N:10]=[CH:9]2)[CH3:18])=[CH:24][CH:23]=1)([CH3:29])[CH3:28])#[N:27]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 3

HCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 112177812-(7-Fluoro-1H-1,3-benzodiazol-1-yl)acetic acidHCID 666490292-[4-(1-Aminoethyl)phenyl]-2-methylpropanenitrile hydrochloride

Produkt 1

HCID 24850277N-{1-[4-(1-Cyano-1-methylethyl)phenyl]ethyl}-2-(7-fluoro-1H-benzimidazol-1-yl)acetamide

Reagenzien, Katalysatoren, Lösungsmittel

2
HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N-{1-[4-(1-Cyano-1-methylethyl)phenyl]ethyl}-2-(7-fluoro-1H-benzimidazol-1-yl)acetamide is synthesized according to example 1 by mixing (7-fluoro-1H-benzimidazol-1-yl)acetic acid (200 mg, 1.03 mmol) prepared according to scheme 5, 2-[4-(1-aminoethyl)phenyl]-2-methylpropanenitrile hydrochloride (231 mg, 1.03 mmol) prepared according to scheme 6, DMAP (249 mg, 2.06 mmol) and HATU (391 mg, 1.03 mmol) in DMF (4.0 mL). The product is purified on HPLCMS: Waters prep LCMS, 27 ml/min, Column: SynerSi (4μ) Polar RP, 21.2×50 mm, Mobile phase: A=water (0.05% TFA) B=MeCN, Gradient used 30% to 50% B in A, in 10 min. The fractions are combined, NaOH 1 N is added and the desired compound is extracted with ethyl acetate. The combined organic fractions are concentrated under reduced pressure to yield the product (226 mg, 0.621 mmol, 60%). 1H NMR (400 MHz, METHANOL-D4) δ ppm 1.48 (d, J=7.03 Hz, 3H) 1.69 (s, 6H) 5.03 (q, J=6.90 Hz, 4H) 5.09 (d, J=16.99 Hz, 1 H) 5.14 (d, J=16.99 Hz, 1H) 7.00 (dd, J=11.43, 8.11 Hz, 1H) 7.20 (td, J=8.11, 4.88 Hz, 1H) 7.37 (d, J=8.20 Hz, 2H) 7.43-7.50 (m, 3H) 8.10 (s, 1H); MS [M+H], calcd: 365.2. found: 365.3.

Aufarbeitung

  1. customprepared
  2. customprepared
  3. customThe product is purified on HPLCMS
  4. additionNaOH 1 N is added
  5. extractionthe desired compound is extracted with ethyl acetate
  6. concentrationThe combined organic fractions are concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-f905888ee4194a04b28e6e3a8501e32c
Quelldatensatz
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08093402B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion