Acetyl chloride → HCID 118021636, compound

HRID 1484514Notes

Reaction equation

HRID 1484514 reaction equation
[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[N:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[O:16][C:17]([F:20])([F:19])[F:18].[C:21](Cl)(=[O:23])[CH3:22]>C(Cl)Cl>[CH3:1][C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[N:12]=[CH:11][C:10]([NH:13][C:21](=[O:23])[CH3:22])=[CH:9][CH:8]=2)=[CH:4][C:3]=1[O:16][C:17]([F:18])([F:20])[F:19]

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 70975647HCID 70975647, compound2×

Product 1

HCID 118021636HCID 118021636, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 6-[4-methyl-3-(trifluoromethoxy)phenoxy]pyridin-3-amine (Intermediate 31, 475 mg, 1.67 mmol) and TEA (0.28 mL) in 5 mL of dry DCM under nitrogen at 0° C., acetyl chloride (0.13 mL) dissolved in 2 mL of dry DCM was added drop wise. The ice bath was then removed and the resulting solution was allowed to stir at room temperature for 30 minutes until complete conversion. Water was added and phases were separated. The organic phase was then washed with an aqueous 15% solution of NaHCO3, dried over Na2SO4, filtered and concentrated to give the title compound (502 mg) as yellow oil.

Workup

  1. additionwas added drop wise
  2. customThe ice bath was then removed
  3. additionWater was added
  4. customphases were separated
  5. washThe organic phase was then washed with an aqueous 15% solution of NaHCO3
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-5ef08165f120456480a8dab1baade43b
Source dataset
uspto-grants-2016_08
Patent number
US09422252B2

Reaction notes

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