Anthranilamide → 2-(2,2-Difluoro-2-(5-fluoropyridin-2-yl)acetamido)benzamide

HRID 473126Notes

Reaction equation

HRID 473126 reaction equation
[F:1][C:2]([F:13])([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[C:3]([O-:5])=O.[Na+].CN(C(ON1N=NC2C=CC=NC1=2)=[N+](C)C)C.F[P-](F)(F)(F)(F)F.[NH2:39][C:40]1[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=1[C:42]([NH2:44])=[O:43]>CN(C=O)C>[F:13][C:2]([F:1])([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][N:7]=1)[C:3]([NH:39][C:40]1[CH:48]=[CH:47][CH:46]=[CH:45][C:41]=1[C:42]([NH2:44])=[O:43])=[O:5]

Participants

5

Reactant 3

HCID 6942AnthranilamideHCID 9886157Methanaminium, N-((dimethylamino)(3H-1,2,3-triazolo(4,5-b)pyridin-3-yloxy)methylene)-N-methyl-, hexafluorophosphate(1-) (1:1)HCID 66609989Sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate

Product 1

HCID 666106942-(2,2-Difluoro-2-(5-fluoropyridin-2-yl)acetamido)benzamideYield 75.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a mixture of sodium 2,2-difluoro-2-(5-fluoropyridin-2-yl)acetate (100 mg, 0.47 mmol), HATU (213 mg, 0.56 mmol) and 2-aminobenzamide (77 mg, 0.56 mmol) was added DMF (2 mL) and the mixture was stirred overnight at rt. The mixture was partitioned between saturated aq ammonium chloride and EtOAc, and the organic layer was concentrated. The residue was purified by silica gel chromotography eluting with 2-10% MeOH/DCM to afford 2-(2,2-difluoro-2-(5-fluoropyridin-2-yl)acetamido)benzamide as an oil (110 mg, 74%). LC-MS (ESI) m/z 332 (M+Na)+.

Workup

  1. customThe mixture was partitioned between saturated aq ammonium chloride and EtOAc
  2. concentrationthe organic layer was concentrated
  3. customThe residue was purified by silica gel chromotography
  4. washeluting with 2-10% MeOH/DCM

Sources & evidence

ORD record
ord-39196647f39e469799b3182b99116ba6
Source dataset
uspto-grants-2014_01
Patent number
US08633207B2

Reaction notes

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