Dimethylformamide → HCID 10100184, compound

HRID 374056Notes

Reaction equation

HRID 374056 reaction equation
[C:1](=O)([O-])[O-].[K+].[K+].[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[NH:15][C:16](=[O:48])[N:17]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30][C:31]1[NH:32][C:33]([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)=[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:35]=1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CI.CN(C)C=O>O1CCCC1.O>[F:7][C:8]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:9]=1[NH:15][C:16](=[O:48])[N:17]([CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][S:30][C:31]1[N:35]([CH3:1])[C:34]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[C:33]([C:42]2[CH:43]=[CH:44][CH:45]=[CH:46][CH:47]=2)[N:32]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 71355Lecimibide

Product 1

HCID 10100184HCID 10100184, compoundYield 52.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of potassium carbonate (0.056 g, 0.00042 mol) in dry tetrahydrofuran (10 mL) was added, portionwise as a solid, N'-(2,4-difluorophenyl)-N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-N-heptylurea (0.25 g, 0.00042 mol) and the reaction mixture was stirred at ambient temperature for 10 minutes. To this reaction mixture was added, dropwise, methyl iodide (0.039 mL, 0.0895 g, 0.00063 mol) and the reaction mixture was stirred for 18 hours at ambient temperature. The reaction mixture was then treated with N,N-dimethylformamide (1.0 mL) and methyl iodide (0.1 mL) and the reaction mixture was stirred at reflux for an additional 24 hours. The reaction mixture was cooled, poured into water and extracted with ethyl acetate. The combined organic extracts were dried over magnesium sulfate and concentrated under vacuum. The residue was chromatographed with 3:7 hexane-ethyl acetate to give the title compound (0.13 g, 0.00022 mol) as a yellow oil. 1H NMR (CDCl3) δ8.1-8.0(m,1H), 7.5-7.1(m,10H), 6.9-6.7(m,2H), 6.4(s,1H), 3.5(s,3H), 3.4-3.2(m,5H), 1.9-1.2(m,17H), 0.9(t,3H,J=8Hz).

Workup

  1. additionTo this reaction mixture was added
  2. stirringthe reaction mixture was stirred
  3. temperatureat reflux for an additional 24 hours
  4. temperatureThe reaction mixture was cooled
  5. extractionextracted with ethyl acetate
  6. dry with materialThe combined organic extracts were dried over magnesium sulfate
  7. concentrationconcentrated under vacuum
  8. customThe residue was chromatographed with 3:7 hexane-ethyl acetate

Sources & evidence

ORD record
ord-ab5d59f3be37450098406ce7a31a4959
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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