Water → N-(2-Amino-5-methoxy-phenyl)-5-bromo-2-fluoro-benzamide

HRID 77077

Reaktionsgleichung

Reaktionsgleichung von HRID 77077
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.Cl.Cl.[CH3:14][O:15][C:16]1[CH:17]=[C:18]([NH2:23])[C:19]([NH2:22])=[CH:20][CH:21]=1.CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.O>ClCCl.CN(C=O)C>[NH2:22][C:19]1[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][C:18]=1[NH:23][C:7](=[O:9])[C:6]1[CH:10]=[C:2]([Br:1])[CH:3]=[CH:4][C:5]=1[F:11]

Komponenten

7

Edukt 4

HCID 962WaterHCID 27363155-Bromo-2-fluorobenzoic acidHCID 30851614-Methoxybenzene-1,2-diamine dihydrochlorideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 63257662N-(2-Amino-5-methoxy-phenyl)-5-bromo-2-fluoro-benzamideAusbeute 62,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Method 6—Step a A mixture of 5-Bromo-2-fluoro-benzoic acid (1.50 g, 6.85 mmol), 4-methoxy-benzene-1,2-diamine dihydrochloride (1.77 g, 8.49 mmol), HATU (2.73 g, 7.19 mmol) and TEA (2.88 mL, 20.76 mmol) in dichloromethane (20 mL) and DMF (5 mL) was stirred at room temperature overnight, then water was added (50 mL), mixture was stirred for 2 h and left standing at room temperature overnight. The precipitate obtained was filtered off and dried to afford 1.45 g of the title compound (50%).

Aufarbeitung

  1. stirringwas stirred for 2 h
  2. waitleft
  3. waitstanding at room temperature overnight
  4. customThe precipitate obtained
  5. filtrationwas filtered off
  6. customdried

Quellen und Nachweise

ORD-Eintrag
ord-d73d945322a94c8a9a3b8a50b768d317
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835648B2

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