4-Methylmorpholine → 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide

HRID 600681

Reaktionsgleichung

Reaktionsgleichung von HRID 600681
[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([OH:14])=O)[CH:5]=[CH:4][N:3]=1.[CH3:19][N:20]1[CH:28]=[C:27]2[C:22]([CH:23]=[C:24]([NH2:29])[CH:25]=[CH:26]2)=[N:21]1.CN1CCOCC1.F[P-](F)(F)(F)(F)F.N1(OC(N(C)C)=[N+](C)C)C2N=CC=CC=2N=N1>CN(C)C=O.C(=O)(O)[O-].[Na+].CC(C)=O.CCCCCC>[Br:1][C:2]1[CH:7]=[C:6]([CH2:8][NH:9][C:10]2[CH:18]=[CH:17][CH:16]=[CH:15][C:11]=2[C:12]([NH:29][C:24]2[CH:25]=[CH:26][C:27]3[C:22]([CH:23]=2)=[N:21][N:20]([CH3:19])[CH:28]=3)=[O:14])[CH:5]=[CH:4][N:3]=1

Komponenten

9

Edukt 4

HCID 79724-MethylmorpholineHCID 5902202-Methyl-2H-indazol-6-amineHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 231189932-[(2-Bromo-pyridin-4-ylmethyl)-amino]benzoic Acid

Produkt 1

HCID 231189722-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamideAusbeute 96 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 180AcetoneLösungsmittelHCID 6228DimethylformamideLösungsmittel2×HCID 8058HexaneLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

0.500 g (1.6 mmol) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-benzoic acid, 0.471 g (3.2 mmol) of 2-methyl-2H-indazol-6-ylamine, 0.4 ml (3.68 mmol) of N-methylmorpholine and 0.729 g (1.92 mmol) of O-(7-azabenzotriazol-1-yl)-1,1,3,3-tetramethyluroniumhexafluorophosphate (HATU) in 25 ml of dimethylformamide are stirred for 16 hours at room temperature. The dimethylformamide is drawn-off in an oil pump vacuum. The remaining residue is drawn off in saturated sodium bicarbonate solution. It is extracted three times with ethyl acetate, and the combined organic phases are dried, filtered and concentrated by evaporation. The residue is chromatographed on silica get with a gradient that consists of hexane:acetone=100:0 to 50:50 as an eluant. 0.669 g (96% of theory) of 2-[(2-bromo-pyridin-4-ylmethyl)-amino]-N-(2-methyl-2H-indazol-6-yl)-benzamide is obtained in the form of a beige foam.

Aufarbeitung

  1. extractionIt is extracted three times with ethyl acetate
  2. customthe combined organic phases are dried
  3. filtrationfiltered
  4. concentrationconcentrated by evaporation
  5. customThe residue is chromatographed on silica
  6. customget with a gradient that

Quellen und Nachweise

ORD-Eintrag
ord-0de3ba5d4743469986fad81892369c95
Quelldatensatz
uspto-grants-2011_03
Patentnummer
US07902229B2

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