Ozone → 2-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyethyl)4methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

HRID 2229324Notes

Reaction equation

HRID 2229324 reaction equation
[O:1]=[O+][O-].[Cl:4][C:5]1[CH:6]=[C:7]([CH3:26])[C:8]2[NH:9][C:10](=[O:25])[C:11]3[CH:21]=[C:20]([CH2:22][CH:23]=C)[CH:19]=[N:18][C:12]=3[N:13]([CH2:16][CH3:17])[C:14]=2[N:15]=1.[BH4-].[Na+].[NH4+].[Cl-]>C(Cl)Cl.CO>[Cl:4][C:5]1[CH:6]=[C:7]([CH3:26])[C:8]2[NH:9][C:10](=[O:25])[C:11]3[CH:21]=[C:20]([CH2:22][CH2:23][OH:1])[CH:19]=[N:18][C:12]=3[N:13]([CH2:16][CH3:17])[C:14]=2[N:15]=1

Participants

7

Reactant 4

HCID 24823OzoneHCID 25517Ammonium ChlorideHCID 4311764Sodium borohydride2×HCID 184666152-Chloro-5,11-dihydro-11-ethyl-4-methyl-8-(2-propenyl)-6h-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-one

Product 1

HCID 184666082-chloro-5,11-dihydro-11-ethyl-8-(2-hydroxyethyl)4methyl-6H-dipyrido[3,2-b:2',3'-e][1,4]diazepin-6-oneYield 74%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

A stream of O3 was introduced into a cold (−78° C.) solution of 2-chloro-5,11-dihydro-11-ethyl-4-methyl-8-(2-propenyl)-6H-dipyrido[3,2-b:2′,3′-e] [1,4]diazepin-6-one (8.04 g, 24.4 mmol) and Sudan III in CH2Cl2 (120 mL) and MeOH (120 mL). When the pink solution turned brown, O2 was bubbled through the solution for 10 min. NaBH4 (1.12 g, 29.4 mmol) was then added and the solution was allowed to warm to room temperature. After 30 min, an additional amount of NaBH4 (500 mg) was added. After 1 h, aqueous saturated NH4Cl was then added and the mixture stirred for 20 min. The solution was concentrated under reduced pressure and extracted with CH2Cl2 (3×). The combined organic extracts were washed with brine, dried (MgSO4), filtered and concentrated under reduced pressure. The residue was purified by flash chromatography (CHCl3:EtOH, 97:3) to give the title compound (6.01 g, 74% yield) as a white solid.

Workup

  1. customO2 was bubbled through the solution for 10 min
  2. waitAfter 1 h
  3. concentrationThe solution was concentrated under reduced pressure
  4. extractionextracted with CH2Cl2 (3×)
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by flash chromatography (CHCl3:EtOH, 97:3)

Sources & evidence

ORD record
ord-6c8878cae1214de1b1b3b3bc326c3f2e
Source dataset
uspto-grants-2002_07
Patent number
US06420359B1

Reaction notes

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