Dimethylformamide → 5-(Benzo[d][1,3]dioxol-5-yl)-3-{6-[3-benzyl-8-(trifluoromet hyl)quinolin-4-yloxy]hexyl}-5-methylimidazolidine-2,4-dione

HRID 1677125Notes

Reaction equation

HRID 1677125 reaction equation
CN(C=O)C.[CH2:6]([C:13]1[CH:14]=[N:15][C:16]2[C:21]([C:22]=1[O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29]Br)=[CH:20][CH:19]=[CH:18][C:17]=2[C:31]([F:34])([F:33])[F:32])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])[O-].[K+].[K+].[O:41]1[C:45]2[CH:46]=[CH:47][C:48]([C:50]3([CH3:57])[NH:54][C:53](=[O:55])[NH:52][C:51]3=[O:56])=[CH:49][C:44]=2[O:43][CH2:42]1>O>[O:41]1[C:45]2[CH:46]=[CH:47][C:48]([C:50]3([CH3:57])[NH:54][C:53](=[O:55])[N:52]([CH2:29][CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][O:23][C:22]4[C:21]5[C:16](=[C:17]([C:31]([F:34])([F:33])[F:32])[CH:18]=[CH:19][CH:20]=5)[N:15]=[CH:14][C:13]=4[CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)[C:51]3=[O:56])=[CH:49][C:44]=2[O:43][CH2:42]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 28298175-(2H-1,3-benzodioxol-5-yl)-5-methylimidazolidine-2,4-dioneHCID 668707273-Benzyl-4-(6-bromohexyloxy)-8-(trifluoromethyl)quinoline

Product 1

HCID 444627495-(Benzo[d][1,3]dioxol-5-yl)-3-{6-[3-benzyl-8-(trifluoromet hyl)quinolin-4-yloxy]hexyl}-5-methylimidazolidine-2,4-dioneYield 121%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A DMF (0.1 mL) solution of 3-benzyl-4-(6-bromohexyloxy)-8-(trifluoromethyl)quinoline (12.5 mg, 0.03 mmol) was added with potassium carbonate (9 mg, 0.06 mmol) and 5-(benzo[d][1,3]dioxol-5-yl)-5-methylimidazolidine-2,4-dione (46.8 mg, 0.20 mmol), and stirred overnight. The reaction solution was added with water, extracted with ethyl acetate, subsequently dried using anhydrous sodium sulfate and concentrated in vacuo. The obtained residue was purified using silica-gel column chromatography (hexane:ethyl acetate), and the title compound (22.5 mg, yield 49%) was obtained as a colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. customsubsequently dried
  3. concentrationconcentrated in vacuo
  4. customThe obtained residue was purified

Sources & evidence

ORD record
ord-ed7a1e0cdd7746e09c3c6b4a552f77ea
Source dataset
uspto-grants-2011_08
Patent number
US08008306B2

Reaction notes

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