Water → HCID 15956292, compound

HRID 356607Notes

Reaction equation

HRID 356607 reaction equation
[H-].[Na+].[CH2:3]([N:5]1[C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[N:8]([CH3:17])[C:7]2[CH:18]=[CH:19][C:20]([C:22]3[CH:26]=[CH:25][NH:24][CH:23]=3)=[N:21][C:6]1=2)[CH3:4].[CH3:27]I.O>CN(C=O)C>[CH2:3]([N:5]1[C:11]2[N:12]=[CH:13][CH:14]=[CH:15][C:10]=2[C:9](=[O:16])[N:8]([CH3:17])[C:7]2[CH:18]=[CH:19][C:20]([C:22]3[CH:26]=[CH:25][N:24]([CH3:27])[CH:23]=3)=[N:21][C:6]1=2)[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 463562HCID 463562, compound

Product 1

HCID 15956292HCID 15956292, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.008 g, 60% in oil) was added to a solution of 5,11-dihydro-11-ethyl-5-methyl-2-(3-pyrrolyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.065 g) in dry DMF (3 mL) and stirred for 30 min. Methyl iodide (0.2 mL) was added and the reaction mixture was stirred for an additional 2 h. Water was added and the product was extracted with CH2Cl2, dried (anhyd Na2SO4), filtered, and evaporated. The residue was chromatographed over silica gel (ethyl acetate/hexanes, 1:1) and was further purified by preparative plate chromatography (ethyl acetate/hexanes, 1:1) to give 0.040 g of the title compound, mp 187°-188° C.

Workup

  1. stirringthe reaction mixture was stirred for an additional 2 h
  2. extractionthe product was extracted with CH2Cl2
  3. dry with materialdried (anhyd Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was chromatographed over silica gel (ethyl acetate/hexanes, 1:1)
  7. customwas further purified by preparative plate chromatography (ethyl acetate/hexanes, 1:1)

Sources & evidence

ORD record
ord-b49561e640034255b5e506a0e199fc73
Source dataset
uspto-grants-1998_11
Patent number
US05837704

Reaction notes

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