Sodium Iodide → HCID 21701300, compound

HRID 1596369Notes

Reaction equation

HRID 1596369 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH3:29])[CH2:5][C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[NH:10][C:9](=[O:17])[CH:8]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)=[O:20])[N:7]=1.[I-].[Na+].Cl[CH2:33][C:34]1[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][N:35]=1>CN(C)C=O>[CH3:3][CH:4]([CH3:29])[CH2:5][C:6]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[N:10]([CH2:33][C:34]2[C:39]([CH3:40])=[CH:38][CH:37]=[CH:36][N:35]=2)[C:9](=[O:17])[CH:8]([NH:18][C:19]([NH:21][C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH3:28])[CH:23]=2)=[O:20])[N:7]=1

Participants

6

Reactant 4

HCID 5238Sodium IodideHCID 24758Sodium hydrideHCID 130586822-(Chloromethyl)-3-methylpyridineHCID 136048889HCID 136048889, compound

Product 1

HCID 21701300HCID 21701300, compoundYield 89.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of sodium hydride (0.027 g of a 64% dispersion in mineral oil) in N,N-dimethylformamide (3 ml) was added gradually N-[(3RS)-2,3-dihydro-5-(2-methylpropyl)-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-(3-methylphenyl)urea (0.200 g) at ambient temperature and the mixture was stirred for 1 hour under the same conditions. To the mixture was added sodium iodide (0.107 g) and followed dropwise a solution of 2-chloromethyl-3-methylpridine (0.093 g,) in N,N-dimethylformamide (2 ml) at the same temperature. The resultant mixture was concentrated in vacuo and the residue was taken up with ethyl acetate and water. The aqueous layer was extracted with another ethyl acetate. The combined organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give a crude compound. The crude compound was recrystallized with isopropyl ether and chloroform to give N-[(3RS)-2,3-dihydro-5-(2-methylpropyl)-1-(3-methylpyridin-2-yl)methyl-2-oxo-1H-1,4-benzodiazepin-3-yl]-N′-(3-methylphenyl)urea (0.23 g) as a colorless powder.

Workup

  1. concentrationThe resultant mixture was concentrated in vacuo
  2. extractionThe aqueous layer was extracted with another ethyl acetate
  3. dry with materialThe combined organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customto give a crude compound
  7. customThe crude compound was recrystallized with isopropyl ether and chloroform

Sources & evidence

ORD record
ord-8c7363c3b8f740abaea465bc2c626608
Source dataset
uspto-grants-2001_09
Patent number
US06291452B1

Reaction notes

Loading…