Sodium Iodide → HCID 19081279, compound

HRID 963485Notes

Reaction equation

HRID 963485 reaction equation
[H-].[Na+].[CH:3]1([C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[NH:13][C:12](=[O:20])[CH:11]([N:21]3[C:25](=[O:26])[C:24]4=[CH:27][CH:28]=[CH:29][CH:30]=[C:23]4[C:22]3=[O:31])[N:10]=2)[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[I-].[Na+].Cl[CH2:35][C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=1>CN(C)C=O.C(O)(=O)C>[CH:3]1([C:9]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[N:13]([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][N:37]=3)[C:12](=[O:20])[CH:11]([N:21]3[C:22](=[O:31])[C:23]4=[CH:30][CH:29]=[CH:28][CH:27]=[C:24]4[C:25]3=[O:26])[N:10]=2)[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 23393Picolyl chlorideHCID 24758Sodium hydrideHCID 135829358HCID 135829358, compound

Product 1

HCID 19081279HCID 19081279, compound

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium hydride (54 mg of a 64% dispersion of mineral oil) in N,N-dimethylformamide (3 ml) was added slowly (3RS)-5-cyclohexyl-2,3-dihydro-3-phthalimido-1H-1,4-benzo-diazepin-2-one (0.50 g) at ambient temperature and the mixture was stirred for 2 hours under the same condition. To the mixture was added sodium iodide (0.213 g) and followed dropwise a solution of 2-chloromethylpyridine (0.213 g) at the same temperature. The mixture was stirred overnight at ambient temperature To the mixture was added acetic acid (0.4 ml) and stirred for 10 minutes. The resultant mixture was concentrated in vacuo and the residue was taken up with ethyl acetate and water. The aqueous layer was alkalined with sodium carbonate and extracted with ethyl acetate. The combined extracts were dried over sodium sulfate, filtered and concentrated in vacuo to give a crude compound. The crude compound was purified by column chromatography on silica gel with a mixture of chloroform and methanol to give (3RS)-5-cyclohexyl-2,3-dihydro-3-phthalimido-1-(pyridin-2-yl)methyl-1H-1,4-benzodiazepin-2-one.

Workup

  1. stirringThe mixture was stirred overnight at ambient temperature To the mixture
  2. stirringstirred for 10 minutes
  3. concentrationThe resultant mixture was concentrated in vacuo
  4. extractionextracted with ethyl acetate
  5. dry with materialThe combined extracts were dried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customto give a crude compound
  9. customThe crude compound was purified by column chromatography on silica gel with a mixture of chloroform and methanol

Sources & evidence

ORD record
ord-dd7917853dff4262b79a34e0e32c6a0f
Source dataset
uspto-grants-1998_06
Patent number
US05763437

Reaction notes

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