1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 22121894, compound

HRID 1858928Notes

Reaction equation

HRID 1858928 reaction equation
Br.[CH3:2][CH:3]1[CH2:9][NH:8][CH2:7][CH2:6][CH:5]([CH3:10])[NH:4]1.C1CCN2C(=NCCC2)CC1.[Cl:22][S:23]([C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[C:28]([CH3:36])=[CH:29][N:30]=[CH:31]2)(=[O:25])=[O:24]>N1C=CC=CC=1>[ClH:22].[CH3:2][CH:3]1[NH:4][CH:5]([CH3:10])[CH2:6][CH2:7][N:8]([S:23]([C:26]2[CH:35]=[CH:34][CH:33]=[C:32]3[C:27]=2[C:28]([CH3:36])=[CH:29][N:30]=[CH:31]3)(=[O:24])=[O:25])[CH2:9]1

Participants

5

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 154871104-Methylisoquinoline-5-sulfonyl chlorideHCID 22121941HCID 22121941, compound

Product 1

HCID 22121894HCID 22121894, compoundYield 54.4%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a suspension of 1.5 g of 2,7-dimethyl-hexahydro-1H-1,4-diazepine hydrobromide obtained in Reference Example 3 in 30 ml of pyridine was added 1.58 g of 1,8-diazabicyclo[5.4.0]-7-undecene, and after addition of 0.84 g of 5-chlorosulfonyl-4-methyl-isoquinoline, the mixture was stirred at room temperature for 1 hour. This reaction mixture was concentrated and the residue was diluted with water, extracted with chloroform, dried, and concentrated. The residue was purified by silica gel column chromatography (chloroform/methanol=30/1) and converted to the hydrochloride in the routine manner to provide 0.70 g of the objective compound (white crystals).

Workup

  1. concentrationThis reaction mixture was concentrated
  2. additionthe residue was diluted with water
  3. extractionextracted with chloroform
  4. customdried
  5. concentrationconcentrated
  6. customThe residue was purified by silica gel column chromatography (chloroform/methanol=30/1)

Sources & evidence

ORD record
ord-6ab3c4db7cd3464296d4875bb033a753
Source dataset
uspto-grants-2000_11
Patent number
US06153608

Reaction notes

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