Ethyl Acetate → N-[5-Cyano-2-((3S)-3-(dimethylamino)pyrrolidin-1-yl)biphenyl-4-yl]-2,2-dimethylpropionamide

HRID 17534Notes

Reaction equation

HRID 17534 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([N:8]2[CH2:12][CH2:11][C@H:10]([N:13]([CH3:15])[CH3:14])[CH2:9]2)[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:4][C:3]=1[C:22]#[N:23].[C:24](Cl)(=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26].C(OCC)(=O)C.[OH-].[Na+]>N1C=CC=CC=1>[C:22]([C:3]1[C:2]([NH:1][C:24](=[O:29])[C:25]([CH3:28])([CH3:27])[CH3:26])=[CH:7][C:6]([N:8]2[CH2:12][CH2:11][C@H:10]([N:13]([CH3:14])[CH3:15])[CH2:9]2)=[C:5]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:4]=1)#[N:23]

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 62493Pivaloyl chlorideHCID 68587091HCID 68587091, compound

Product 1

HCID 68584926N-[5-Cyano-2-((3S)-3-(dimethylamino)pyrrolidin-1-yl)biphenyl-4-yl]-2,2-dimethylpropionamideYield 95.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Amino-6-[(3S)-3-(dimethylamino)pyrrolidin-1-yl]biphenyl-3-carbonitrile (I-243) (300 mg, 0.98 mmol) was dissolved in pyridine (3 ml), and under nitrogen atmosphere at room temperature, pivaloyl chloride (181 μl, 1.47 mmol) was added. After stirring at room temperature for 3 days, the reaction liquid was fractionated with ethyl acetate and aqueous 1 M sodium hydroxide solution. The organic layer was washed with saturated brine, then dried over anhydrous sodium sulfate. The insoluble matter was separated by filtration, then the solvent was evaporated away and the resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:methanol=98:2) to obtain the entitled compound (364 mg, 95%) as a pale yellow gel.

Workup

  1. customthe reaction liquid
  2. washThe organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe insoluble matter was separated by filtration
  5. customthe solvent was evaporated away
  6. customthe resulting residue was purified by middle-pressure liquid chromatography (eluent, chloroform:methanol=98:2)

Sources & evidence

ORD record
ord-a94c1e8e44844ea390683d492e0d9e4a
Source dataset
uspto-grants-2010_06
Patent number
US07737166B2

Reaction notes

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