Ethyl Acetate → HCID 9893833, compound

HRID 2379894Notes

Reaction equation

HRID 2379894 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([S:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[NH:10][C:11]=2[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[C:38]([O:41][CH2:42][CH3:43])(=O)C>CN(C)C=O>[O:41]1[C:42]2[CH:43]=[CH:3][CH:2]=[CH:1][C:7]=2[N:8]=[C:38]1[N:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][S:18][C:9]1[NH:8][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[N:10]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 10048624N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine

Product 1

HCID 9893833HCID 9893833, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Method A, Part B. A solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine (prepared according to the procedure of U.S. patent application Ser. No. 07/416,606, Billheimer et al. ) (8.57 g, 19.7 mmol), the sulfone prepared in Method A, Part A above (3.52 g, 17.9 mmol) and potassium carbonate (3.00 g, 21.7 mmol) in dimethylformamide (30 mL) was heated to 90° C. for 18 hours. The mixture was allowed to cool and poured into ethyl acetate (200 mL). This solution was washed with water (4×200 mL), and the water washings were back-extracted in sequence with ethyl acetate (200 mL). The organic phases were combined, dried over anhydrous magnesium sulfate, filtered and evaporated. The residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane), and the title product was obtained as a foam from evaporation from heptane solution, m.p. 58°-60° C. (7.00 g, 12.7 mmol, 71%). 1H NMR (CDCl3): 10.77 (1H, br s); 7.61-6.84 (14H, m); 3.52-3.40 (4H, m); 3.04 (2H, t, J=7.2 Hz); 1.79-1.58 (6H, m); 1.53-1.40 (2H, m); 1.37-1.21 (8H, m); 0.87 (3H, t, J=6.6 Hz). High-resolution mass spectrum: for C34H40N4OS, calc. 552.2923, obs. 552.2925, diff. 0.4 ppm.

Workup

  1. temperatureto cool
  2. washThis solution was washed with water (4×200 mL)
  3. extractionthe water washings were back-extracted in sequence with ethyl acetate (200 mL)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residual oil was separated by flash chromatography (1:4 ethyl acetate-hexane)

Sources & evidence

ORD record
ord-b469d63f92204bc89e6a0ac1e2a177f9
Source dataset
uspto-grants-1994_11
Patent number
US05364875

Reaction notes

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