Sodium Iodide → (3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(3-methylpyridin-2-yl)methyl-3-phtalimido-1H-1,4-benzodiazepin-2-one

HRID 963472Notes

Reaction equation

HRID 963472 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[NH:14][C:13](=[O:21])[CH:12]([N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])[N:11]=1.[I-].[Na+].Cl[CH2:36][C:37]1[C:42]([CH3:43])=[CH:41][CH:40]=[CH:39][N:38]=1>CN(C)C=O>[F:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[N:14]([CH2:36][C:37]2[C:42]([CH3:43])=[CH:41][CH:40]=[CH:39][N:38]=2)[C:13](=[O:21])[CH:12]([N:22]2[C:23](=[O:32])[C:24]3=[CH:31][CH:30]=[CH:29][CH:28]=[C:25]3[C:26]2=[O:27])[N:11]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 130586822-(Chloromethyl)-3-methylpyridineHCID 19081136(3RS)-2,3-dihydro-5-(2-fluorophenyl)-3-phthalimido-1H-1,4-benzodiazepin-2-one

Product 1

HCID 19081220(3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(3-methylpyridin-2-yl)methyl-3-phtalimido-1H-1,4-benzodiazepin-2-oneYield 98.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.11 g of a 64% dispersion in mineral oil) in dry N,N-dimethylformamide (10 ml) was added (3RS)-2,3-dihydro-5-(2-fluorophenyl)-3-phthalimido-1H-1,4-benzodiazepin-2-one (1.00 g) under stirring for 2 hours at ambient temperature. To the mixture was added sodium iodide (0.42 g) and followed dropwise a solution of 2-chloromethyl-3-methyl-pyridine (0.389 g) in dry N,N-dimethylformamide (3 ml) at ambient temperature. The mixture was stirred overnight at room temperature. The mixture was concentrated in vacuo, and the residue was taken up with ethyl acetate. The organic layer was washed with saturated sodium carbonate aqueous solution, dried over sodium sulfate, filtered and concentrated in vacuo to give (3RS)-2,3-dihydro-5-(2-fluorophenyl)-1-(3-methylpyridin-2-yl)methyl-3-phtalimido-1H-1,4-benzodiazepin-2-one (1.24 g). The product was used in a following reaction step without further purification.

Workup

  1. customat ambient temperature
  2. stirringThe mixture was stirred overnight at room temperature
  3. concentrationThe mixture was concentrated in vacuo
  4. washThe organic layer was washed with saturated sodium carbonate aqueous solution
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9217c60e79064a349628d09d0779f5b9
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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