1,1'-Thiocarbonyldiimidazole → 1,2,3,4-Tetrahydro-2-(imidazol-1-yl)thiocarbonyl-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

HRID 2415375Notes

Reaction equation

HRID 2415375 reaction equation
[C:1](N1C=CN=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[S:2].[CH2:13]1[O:21][C:20]2[CH:19]=[CH:18][C:17]([CH:22]3[C:26]4[NH:27][C:28]5[CH:29]=[CH:30][CH:31]=[CH:32][C:33]=5[C:34](=[O:35])[C:25]=4[CH2:24][NH:23]3)=[CH:16][C:15]=2[O:14]1>CN(C=O)C.O>[N:3]1([C:1]([N:23]2[CH2:24][C:25]3[C:34](=[O:35])[C:33]4[CH:32]=[CH:31][CH:30]=[CH:29][C:28]=4[NH:27][C:26]=3[CH:22]2[C:17]2[CH:18]=[CH:19][C:20]3[O:21][CH2:13][O:14][C:15]=3[CH:16]=2)=[S:2])[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

5

Reactant 2

HCID 802641,1'-ThiocarbonyldiimidazoleHCID 108921213-(1,3-benzodioxol-5-yl)-1,2,3,4-tetrahydro-9H-pyrrolo[3,4-b]quinolin-9-one

Product 1

HCID 129930301,2,3,4-Tetrahydro-2-(imidazol-1-yl)thiocarbonyl-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a suspension of 1,1′-thiocarbonyldiimidazole (0.192 g, 1.08 mmol) in DMF (5 mL, anhydrous) at 0° C. was added 1,2,3,4-tetrahydro-3-(3,4-methylenedioxyphenyl)-9H-pyrrolo-[3,4-b]quinolin-9-one (0.30 g, 0.98 mmol) (prepared as in Example 5). The mixture warmed to room temperature and stirred for 20 h. The solution was diluted with water and extracted into ethyl acetate. The organic layers were combined and washed with aq. NaHCO3 and brine, dried with MgSO4 and concentrated in vacuo, to yield the product as a light tan solid.

Workup

  1. extractionextracted into ethyl acetate
  2. washwashed with aq. NaHCO3 and brine
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b10c9edfbd1f4ba490bffdcce6cff226
Source dataset
uspto-grants-2004_11
Patent number
US06818646B2

Reaction notes

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