Pyridine → HCID 70223319, compound

HRID 1532510Notes

Reaction equation

HRID 1532510 reaction equation
[F:1][CH:2]([F:36])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([NH:28][CH2:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:21]=[CH:20][N:19]=[CH:18][CH:17]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].N1C=CC=CC=1.[C:43](OC(=O)C)(=[O:45])[CH3:44]>ClCCCl.CN(C1C=CN=CC=1)C>[F:36][CH:2]([F:1])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:22]2[CH:23]=[N:24][C:25]([N:28]([CH2:29][C:30]3[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=3)[C:43](=[O:45])[CH3:44])=[CH:26][CH:27]=2)[CH2:15][C:16]2[CH:17]=[CH:18][N:19]=[CH:20][CH:21]=2)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:12])[F:13]

Participants

6

Reactant 3

HCID 1049PyridineHCID 7918Acetic AnhydrideHCID 9870470HCID 9870470, compound

Product 1

HCID 70223319HCID 70223319, compoundYield 27%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 4-(2-[3,4-Bis(difluoromethoxy)phenyl]-2-[6-(benzylamino)3-pyridyl]ethyl)pyridine from Example 1 (100 mg, 0.2 mmol) in 3 mL of 1,2-dichloroethane, was added 0.077 mL (0.96 mmol) of pyridine followed by 0.012 mg (0.1 mmol) of DMAP and 0.056 mL (0.6 mmol) of acetic anhydride. The solution was stirred 24 h at reflux, quenched with water and diluted with CH2Cl2. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by chromatography on silica gel (Gradient 100% ethyl acetate to 10% EtOH/ethyl acetate) to afford 29 mg (27%) of the acetamide.

Workup

  1. temperatureat reflux
  2. customquenched with water
  3. additiondiluted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by chromatography on silica gel (Gradient 100% ethyl acetate to 10% EtOH/ethyl acetate)

Sources & evidence

ORD record
ord-b63fa4e5663e4ac7ac59915be5a625f8
Source dataset
uspto-grants-2001_03
Patent number
US06200993B1

Reaction notes

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