Diisopropylethylamine → 4-Acetyl-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-morpholinecarboxamide

HRID 42251

Reaktionsgleichung

Reaktionsgleichung von HRID 42251
CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[C:25]([N:28]1[CH2:33][CH2:32][O:31][CH:30]([C:34]([OH:36])=O)[CH2:29]1)(=[O:27])[CH3:26].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>[C:25]([N:28]1[CH2:33][CH2:32][O:31][CH:30]([C:34]([NH:64][C:57]2[CH:56]=[C:55]([C:50]3[CH:51]=[CH:52][CH:53]=[C:54]4[C:49]=3[CH:48]=[CH:47][NH:46]4)[CH:63]=[C:62]3[C:58]=2[CH:59]=[N:60][NH:61]3)=[O:36])[CH2:29]1)(=[O:27])[CH3:26]

Komponenten

6

Edukt 4

HCID 81531DiisopropylethylamineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 205980784-Acetylmorpholine-2-carboxylic acidHCID 582680196-(1H-indol-4-yl)-1H-indazol-4-amine

Produkt 1

HCID 445403114-Acetyl-N-[6-(1H-indol-4-yl)-1H-indazol-4-yl]-2-morpholinecarboxamideAusbeute 30,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of HATU (0.107 g, 0.28 mmol) in dry DMF (3 ml) was added 4-acetyl-2-morpholinecarboxylic acid (0.05 g, 0.282 mmol). DIPEA (0.098 ml, 0.56 mmol) was added and the mixture was left to stand for 10 min. 6-(1H-indol-4-yl)-1H-indazol-4-amine (0.04 g, 0.14 mmol), dissolved in dry DMF (3 ml) was added and the solution was left to stand at room temperature for 20 hr. DMF was removed by blow down under a stream of nitrogen, then the residue was dissolved and purified by Mass Directed AutoPrep Method B. The solvent was removed in vacuo and product dried in a vacuum oven at 50° C. overnight to give the title compound as a brown oil (17 mg).

Aufarbeitung

  1. waitthe mixture was left
  2. additionwas added
  3. waitthe solution was left
  4. waitto stand at room temperature for 20 hr
  5. customDMF was removed by blow down under a stream of nitrogen
  6. dissolutionthe residue was dissolved
  7. custompurified by Mass Directed AutoPrep Method B
  8. customThe solvent was removed in vacuo and product
  9. customdried in a vacuum oven at 50° C. overnight

Quellen und Nachweise

ORD-Eintrag
ord-9c46e66f17024e1990e7244b6b765a50
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536169B2

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