Ammonia → 2-[2,4-Difluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetamide

HRID 1771777Notes

Reaction equation

HRID 1771777 reaction equation
[F:1][C:2]1[C:15]([NH:16][CH2:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)[CH:21]=[CH:20][C:19]=2[F:31])=[C:14]([F:32])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6](OC(C)C)=[O:7].[NH3:33]>O1CCOCC1>[F:1][C:2]1[C:15]([NH:16][CH2:17][C:18]2[CH:23]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([F:30])[CH:25]=3)[CH:21]=[CH:20][C:19]=2[F:31])=[C:14]([F:32])[CH:13]=[CH:12][C:3]=1[O:4][CH2:5][C:6]([NH2:33])=[O:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 71503443US9249085, II(d)

Product 1

HCID 894440472-[2,4-Difluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetamideYield 36%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of isopropyl 2-[2,4-difluoro-3-[[2-fluoro-5-(3-fluorophenyl)phenyl]methylamino]phenoxy]acetate (II(d)) (1.0 g, 2.24 mmol, 1.0 eq) in dioxane (10 mL) was added NH3 (35% aqueous solution, 30 mL). The reaction was then heated to 100° C. and stirred overnight. The resulting mixture was concentrated in vacuo. Water was added and the aqueous layer was extracted with EtOAc. The organic extract was washed with water and brine, dried (Na2SO4), filtered and evaporated in vacuo to give the title compound as a white solid (320 mg, 36%).

Workup

  1. concentrationThe resulting mixture was concentrated in vacuo
  2. additionWater was added
  3. extractionthe aqueous layer was extracted with EtOAc
  4. extractionThe organic extract
  5. washwas washed with water and brine
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-957672727e5e4b6fb0ca600bd3fa0a21
Source dataset
uspto-grants-2016_02
Patent number
US09249085B2

Reaction notes

Loading…