2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-vinyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one → HCID 10639163, compound

HRID 724964Notes

Reaction equation

HRID 724964 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH:19]=C)[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1.ClCCl.C[OH:27]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([CH3:22])[C:7](=[O:21])[C:8]3[CH:18]=[C:17]([CH:19]=[O:27])[CH:16]=[N:15][C:9]=3[N:10]([CH2:13][CH3:14])[C:11]=2[N:12]=1

Participants

3

Reactant 2

HCID 197111422-chloro-5,11-dihydro-11-ethyl-5-methyl-8-vinyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneHCID 21226129Dichloromethane methanol

Product 1

HCID 10639163HCID 10639163, compoundYield 81%

Conditions

Temperature
-78 °C

Procedure

The 2-chloro-5,11-dihydro-11-ethyl-5-methyl-8-vinyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one (2.34 g, 7.43 mmol) was dissolved in 1:1 dichloromethane/methanol (40 mL) and cooled to -78° C. This solution was then saturated with ozone and a stream ozone was bubbled through for 10 minutes while stirring. The mixture was warmed to ambient temperature and quenched with excess dimethylsulfide. The mixture was then concentrated and the resulting residue was purified by flash chromatography (gradient of hexanes to 1:1 hexanes/ethyl acetate) to give the title compound (1.9 g, 81%), m.p. 199°-201° C.

Workup

  1. customsaturated with ozone and a stream ozone was bubbled through for 10 minutes
  2. temperatureThe mixture was warmed to ambient temperature
  3. customquenched with excess dimethylsulfide
  4. concentrationThe mixture was then concentrated
  5. customthe resulting residue was purified by flash chromatography (gradient of hexanes to 1:1 hexanes/ethyl acetate)

Sources & evidence

ORD record
ord-bf00fc2d31894110870a241c65e2e847
Source dataset
uspto-grants-1998_01
Patent number
US05705499

Reaction notes

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