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

HRID 77079

Reaktionsgleichung

Reaktionsgleichung von HRID 77079
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([F:11])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.[Cl:12][C:13]1[CH:14]=[C:15]([NH2:20])[C:16]([NH2:19])=[CH:17][CH:18]=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>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([Cl:12])=[CH:14][C:15]=1[NH:20][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 72634-Chloro-1,2-diaminobenzeneHCID 27363155-Bromo-2-fluorobenzoic acidHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)

Produkt 1

HCID 24699699N-(2-Amino-5-chloro-phenyl)-5-bromo-2-fluoro-benzamideAusbeute 52 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

Method 7—Step a A mixture of 5-Bromo-2-fluoro-benzoic acid (3.00 g, 13.70 mmol), 4-chloro-benzene-1,2-diamine (2.42 g, 16.99 mmol), HATU (5.47 g, 14.38 mmol) and TEA (1.91 mL, 13.83 mmol) in dichloromethane (70 mL) and DMF (16 mL) was stirred at room temperature overnight, then water was added (80 mL) and left standing at room temperature overnight. The organic layer was divided and solvent removed under reduced pressure and the crude oil obtained was crystallized from the mixture of solvents dichloromethane:cyclohexane/3:1 (30 mL) to afford 2.19 g of the title compound (52%).

Aufarbeitung

  1. waitleft
  2. waitstanding at room temperature overnight
  3. customsolvent removed under reduced pressure
  4. customthe crude oil obtained
  5. customwas crystallized from the mixture of solvents dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-b4ce010ef34c425eb8d782dbd571233d
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08835648B2

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