1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 9843461, compound

HRID 1599440Notes

Reaction equation

HRID 1599440 reaction equation
[CH:1]([S:4](Cl)(=[O:6])=[O:5])([CH3:3])[CH3:2].[CH2:8]([N:15]1[C:24](=[O:25])[CH2:23][C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Cl:26])[CH:21]=2)[C:16]1=[O:27])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.C1CCN2C(=NCCC2)CC1>C(Cl)Cl.CCOC(C)=O>[CH2:8]([N:15]1[C:24](=[O:25])[CH:23]([S:4]([CH:1]([CH3:3])[CH3:2])(=[O:6])=[O:5])[C:22]2[C:17](=[CH:18][CH:19]=[C:20]([Cl:26])[CH:21]=2)[C:16]1=[O:27])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 824082-Propanesulfonyl chlorideHCID 11011573HCID 11011573, compound

Product 1

HCID 9843461HCID 9843461, compoundYield 54.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Isopropylsulfonyl chloride (140 mg, 0.962mmol) was added to a solution of 250 mg (0.875 mmol) 2-benzyl-6-chloro-4H-isoquinoline-1,3-dione and 270 mg (1.75 mmol) DBU in 2.5 mL methylene chloride under Argon, which was cooled in ice-EtOH to -10° C. After 30 min, the reaction was allowed to warm to room temperature and was stirred overnight. The reaction was diluted with EtOAc, washed three times with 2N HCl dried (Na2 SO4) and concentrated. The residue was triturated with EtOH, petroleum ether was added and the resulting crystals were filtered. Recrystallization from MeOH-petroleum ether gave 186 mg of the title compound, mp 150°-152° C.

Workup

  1. washwashed three times with 2N HCl
  2. customdried (Na2 SO4)
  3. concentrationconcentrated
  4. customThe residue was triturated with EtOH, petroleum ether
  5. additionwas added
  6. filtrationthe resulting crystals were filtered
  7. customRecrystallization from MeOH-petroleum ether

Sources & evidence

ORD record
ord-cefdf3befced4d6d93f7e20ffcaf7d75
Source dataset
uspto-grants-1998_04
Patent number
US05741798

Reaction notes

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