Water → HCID 15956286, compound

HRID 356605Notes

Reaction equation

HRID 356605 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[NH:23][CH:24]=[CH:25][CH:26]=3)=[N:21][C:6]1=2)[CH3:4].[C:27](Cl)(=[O:29])[CH3:28].O>CN(C=O)C>[C:27]([N:23]1[CH:24]=[CH:25][CH:26]=[C:22]1[C:20]1[CH:19]=[CH:18][C:7]2[N:8]([CH3:17])[C:9](=[O:16])[C:10]3[CH:15]=[CH:14][CH:13]=[N:12][C:11]=3[N:5]([CH2:3][CH3:4])[C:6]=2[N:21]=1)(=[O:29])[CH3:28]

Participants

6

Reactant 4

HCID 962WaterHCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 463561Dipyridodiazepinone deriv. 41

Product 1

HCID 15956286HCID 15956286, compoundYield 15.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Sodium hydride (0.013 g, 60% in oil) was added to a solution of 5,11-dihydro-11-ethyl-5-methyl-2-(2-pyrrolyl)-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (0.100 g) in dry DMF (3 mL) and stirred for 30 min. After cooling to 0° C., acetyl chloride (0.025 g) was added and the reaction mixture was allowed to warm to room temperature overnight. Water was added and the product was extracted with CH2Cl2, dried (anhyd Na2SO4), filtered, and evaporated. The residue was purified by preparative plate chromatography (ethyl acetate/hexanes, 1:1). Crystallization from ethyl acetate/pet ether gave 0.018 g of the title compound, mp 106°-108° C.

Workup

  1. temperatureto warm to room temperature overnight
  2. extractionthe product was extracted with CH2Cl2
  3. dry with materialdried (anhyd Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by preparative plate chromatography (ethyl acetate/hexanes, 1:1)
  7. customCrystallization from ethyl acetate/pet ether

Sources & evidence

ORD record
ord-9692b0225cea4f658c06c6575ef6eefb
Source dataset
uspto-grants-1998_11
Patent number
US05837704

Reaction notes

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