Hydrochloric Acid → N-(5-Cyano-2-fluoro-4-methoxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide

HRID 17526Notes

Reaction equation

HRID 17526 reaction equation
[NH2:1][C:2]1[C:3]([O:18][CH3:19])=[C:4]([C:16]#[N:17])[C:5]([CH3:15])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:7]=1[F:8].[C:20](Cl)(=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22].Cl>N1C=CC=CC=1>[C:16]([C:4]1[C:3]([O:18][CH3:19])=[C:2]([NH:1][C:20](=[O:25])[C:21]([CH3:24])([CH3:23])[CH3:22])[C:7]([F:8])=[C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[C:5]=1[CH3:15])#[N:17]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 62493Pivaloyl chlorideHCID 860975095-Amino-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile

Product 1

HCID 86630868N-(5-Cyano-2-fluoro-4-methoxy-6-methylbiphenyl-3-yl)-2,2-dimethylpropionamide

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

5-Amino-6-fluoro-4-methoxy-2-methylbiphenyl-3-carbonitrile (I-236) (300 mg, 1.17 mmol) was dissolved in pyridine (3 ml), and under nitrogen atmosphere at 0° C., pivaloyl chloride (433 μl, 3.51 mmol) was dropwise added. After stirring at roam temperature for 20 hours, aqueous 1 M hydrochloric acid solution was added to the reaction liquid at 0° C. The solution was extracted twice with ethyl acetate. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate.

Workup

  1. extractionThe solution was extracted twice with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate

Sources & evidence

ORD record
ord-b7d31a10c76446828935736c15535c06
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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