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

HRID 77079

Reaction equation

HRID 77079 reaction equation
[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]

Participants

7

Reactant 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)

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-b4ce010ef34c425eb8d782dbd571233d
Source dataset
uspto-grants-2014_09
Patent number
US08835648B2

Linked notes

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