Sodium hydride → HCID 86705172, compound

HRID 2401268Notes

Reaction equation

HRID 2401268 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([N:11]2[CH2:15][C@H:14]([CH2:16][CH2:17][CH3:18])[NH:13][C:12]2=[O:19])=[CH:7][CH:6]=1.Cl[CH2:21][C:22]([NH:24][C:25]1[CH:30]=[C:29]([C:31]([F:34])([F:33])[F:32])[CH:28]=[CH:27][N:26]=1)=[O:23]>CN(C=O)C>[CH3:3][O:4][C:5]1[CH:6]=[CH:7][C:8]([N:11]2[CH2:15][C@H:14]([CH2:16][CH2:17][CH3:18])[N:13]([CH2:21][C:22]([NH:24][C:25]3[CH:30]=[C:29]([C:31]([F:34])([F:32])[F:33])[CH:28]=[CH:27][N:26]=3)=[O:23])[C:12]2=[O:19])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 86705170HCID 86705170, compoundHCID 131731729HCID 131731729, compound

Product 1

HCID 86705172HCID 86705172, compoundYield 31.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (60%, 27 mg) was added to a solution of (4S)-1-(4-methoxyphenyl)-4-propylimidazolidin-2-one (32 mg) in DMF (1.5 mL), and the mixture was stirred at room temperature for 15 min. To the mixture was added 2-chloro-N-[4-(trifluoromethyl)pyridin-2-yl]acetamide (39 mg), and the resulting mixture was stirred for 15 hr. Thereafter, the reaction mixture was subjected to filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by preparative HPLC, and further the resulting solid was washed with isopropyl ether to afford 2-[(55)-3-(4-methoxyphenyl)-2-oxo-5-propylimidazolidin-1-yl]-N-[4-(trifluoromethyl)pyridin-2-yl]acetamide (19 mg).

Workup

  1. stirringthe resulting mixture was stirred for 15 hr
  2. filtrationThereafter, the reaction mixture was subjected to filtration
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by preparative HPLC
  5. washfurther the resulting solid was washed with isopropyl ether

Sources & evidence

ORD record
ord-ac7182753e0d4dd3a5cb25b3c2b143d5
Source dataset
uspto-grants-2014_08
Patent number
US08796272B2

Reaction notes

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