Diisopropylethylamine → N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-5-methyl-2-(methyloxy)benzamide

HRID 42247

Reaktionsgleichung

Reaktionsgleichung von HRID 42247
[CH3:1][C:2]1[CH:3]=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.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>[NH:46]1[C:54]2[C:49](=[C:50]([C:55]3[CH:63]=[C:62]4[C:58]([CH:59]=[N:60][NH:61]4)=[C:57]([NH:64][C:7](=[O:9])[C:6]4[CH:10]=[C:2]([CH3:1])[CH:3]=[CH:4][C:5]=4[O:11][CH3:12])[CH:56]=3)[CH:51]=[CH:52][CH:53]=2)[CH:48]=[CH:47]1

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 5201672-Methoxy-5-methylbenzoic acidHCID 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 44540224N-[6-(1H-Indol-4-yl)-1H-indazol-4-yl]-5-methyl-2-(methyloxy)benzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 5-methyl-2-(methyloxy)benzoic acid (67 mg, 0.40 mmol) in DMF (1 ml), HATU (248 mg, 0.40 mmol) and DIPEA (156 mg, 1.208 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 for 3 h then it was loaded onto a PS-aminopropyl cartridge 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. The solvent was dried under a stream of nitrogen. The residue was dissolved in DMSO and further purified by HPLC using the following conditions:

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. customThe solvent was dried under a stream of nitrogen
  7. dissolutionThe residue was dissolved in DMSO
  8. customfurther purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-418e8f9161d04a56b0b204662184b67a
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536169B2

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