2-Ethoxybenzoic acid → 2-(Ethyloxy)-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide

HRID 42250

Reaktionsgleichung

Reaktionsgleichung von HRID 42250
[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([OH:8])=O)[CH3:2].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.CCN(C(C)C)C(C)C.[NH:46]1[C:54]2[C:49](=[C:50]([C:55]3[CH:56]=[C:57]([NH2:64])[C:58]4[CH:59]=[N:60][NH:61][C:62]=4[CH:63]=3)[CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47]1>CN(C=O)C>[CH2:1]([O:3][C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6]([NH:64][C:57]1[CH:56]=[C:55]([C:50]2[CH:51]=[CH:52][CH:53]=[C:54]3[C:49]=2[CH:48]=[CH:47][NH:46]3)[CH:63]=[C:62]2[C:58]=1[CH:59]=[N:60][NH:61]2)=[O:8])[CH3:2]

Komponenten

6

Edukt 4

HCID 672522-Ethoxybenzoic acidHCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Produkt 1

HCID 445403102-(Ethyloxy)-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 2-(ethyloxy)benzoic acid (67 mg, 0.40 mmol) in DMF (1 ml), HATU (248 mg, 0.40 mmol) and DIPEA (0.211 mL, 1.21 mmol) were added. The reaction was stirred for 30 mins under nitrogen before addition of 6-(1H-indol-4-yl)-1H-indazol-4-amine (50 mg, 0.20 mmol). The reaction was stirred overnight then it was loaded onto a PS-aminopropyl cartridge (5 g) and left for 3 h. The cartridge was washed with 10% MeOH in DCM. Appropriate fractions were combined and the solvent was evaporated. The residue was dissolved in MeOH:DMSO (1 ml; 1:1, v/v) and purified by Mass Directed Automated Preparative HPLC using method B. Appropriate fractions were dried under a stream of nitrogen to give title compound, 27 mg.

Aufarbeitung

  1. waitleft for 3 h
  2. washThe cartridge was washed with 10% MeOH in DCM
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in MeOH
  5. custom1:1, v/v) and purified by Mass Directed Automated Preparative HPLC
  6. customAppropriate fractions were dried under a stream of nitrogen

Quellen und Nachweise

ORD-Eintrag
ord-cab91de482c944419f7d48679e95dcd9
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536169B2

Verknüpfte Notizen

Wird geladen…