4-Fluorobenzonitrile → HCID 69944125, compound

HRID 1934699Notes

Reaction equation

HRID 1934699 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:23][C@@H:24]([CH3:27])[CH2:25][OH:26])=[C:7]([CH:22]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[O:9])#[N:2].[H-].[Na+].F[C:31]1[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=1>CN(C)C=O.C(OCC)(=O)C>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([NH:23][C@@H:24]([CH3:27])[CH2:25][O:26][C:31]2[CH:38]=[CH:37][C:34]([C:35]#[N:36])=[CH:33][CH:32]=2)=[C:7]([CH:22]=1)[C:8]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=1)=[O:9])#[N:2]

Participants

6

Reactant 3

HCID 145174-FluorobenzonitrileHCID 24758Sodium hydrideHCID 54513542HCID 54513542, compound

Product 1

HCID 69944125HCID 69944125, compoundYield 33.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)-5-cyano-N-(3,4-dimethoxybenzyl)-2-(2-hydroxy-1-methylethylamino)benzamide (177 mg) in dimethylformamide (4 mL) was added sodium hydride (19.2 mg) at ambient temperature. After stirring for 20 minutes, 4-fluorobenzonitrile (63.8 mg) was added to the mixture. After stirring for an hour at 60° C., the mixture was diluted with ethyl acetate and washed successively with water and brine. The organic layer was dried over sodium sulfate and evaporated in vacuo. The residue was subjected to a silica gel column chromatography eluting with the mixture of chloroform and ethyl acetate (9:1) to give (S)-5-cyano-2-[2-(4-cyanophenoxy)-1-methylethylamino]-N-(3,4-dimethoxybenzyl)benzamide (76 mg) as a solid substance.

Workup

  1. stirringAfter stirring for an hour at 60° C.
  2. washwashed successively with water and brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. customevaporated in vacuo
  5. washeluting with the mixture of chloroform and ethyl acetate (9:1)

Sources & evidence

ORD record
ord-549406a690954975bceb14187633f125
Source dataset
uspto-grants-2002_05
Patent number
US06384080B1

Reaction notes

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