Anthranilamide → HCID 66609019, compound

HRID 473170Notes

Reaction equation

HRID 473170 reaction equation
[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[C:3]([OH:5])=O.C(Cl)Cl.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH2:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH2:32])=[O:31]>N1C=CC=CC=1>[Br:1][CH:2]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[C:3]([NH:27][C:28]1[CH:36]=[CH:35][CH:34]=[CH:33][C:29]=1[C:30]([NH2:32])=[O:31])=[O:5]

Participants

6

Reactant 4

HCID 6942AnthranilamideHCID 65578Oxalyl chlorideHCID 22350042dichloromethane N,N-dimethylformamideHCID 86662700HCID 86662700, compound

Product 1

HCID 66609019HCID 66609019, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a 0.5 M solution of 2-bromo-2-(5-fluoropyridin-2-yl)acetic acid in 99:1 DCM/DMF is added oxalyl chloride (1.2 equiv) and the mixture is allowed to stir at rt for 30 min or until the reaction is substantially complete. The mixture is then cooled to 0° C. and 2-aminobenzamide (1 equiv) in pyridine (2 mL) is added slowly, and the mixture is allowed to warm to rt over ca. 1 h. The mixture is concentrated under reduced pressure and the residue is purified by chromatography to afford 2-(2-bromo-2-(5-fluoropyridin-2-yl)acetamido)benzamide.

Workup

  1. temperatureThe mixture is then cooled to 0° C.
  2. temperatureto warm to rt over ca. 1 h
  3. concentrationThe mixture is concentrated under reduced pressure
  4. customthe residue is purified by chromatography

Sources & evidence

ORD record
ord-5e2e24197f2e4426b11b2f699580d076
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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