Dicyclohexylcarbodiimide → 2-(2,4-Difluoro-phenyl)-N-[5-(4,5-diphenyl-1H-imidazol-2-ylsulfanyl)-pentyl]-N-heptyl-acetamide

HRID 1109072Notes

Reaction equation

HRID 1109072 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.O.ON1C2C=CC=CC=2N=N1.[F:43][C:44]1[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=1[CH2:51][C:52]([OH:54])=O.C1(N=C=NC2CCCCC2)CCCCC1>CN(C)C=O>[F:43][C:44]1[CH:49]=[C:48]([F:50])[CH:47]=[CH:46][C:45]=1[CH2:51][C:52]([N:24]([CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][S:18][C:9]1[NH:10][C:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)=[C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[N:8]=1)[CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])=[O:54]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 1235812,4-Difluorophenylacetic acidHCID 27960291-Hydroxybenzotriazole hydrateHCID 10048624N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-heptanamine

Product 1

HCID 100999372-(2,4-Difluoro-phenyl)-N-[5-(4,5-diphenyl-1H-imidazol-2-ylsulfanyl)-pentyl]-N-heptyl-acetamideYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-[5-(4,5-diphenyl-1H-imidazol-2-ylthio)pentyl]-1-heptanamine (2.2 g, 0.005 mol), 1-hydroxybenzotriazole hydrate (0.81 g, 0.006 mol), and 2,4-difluorophenylacetic acid (1.12 g, 0. 0065 mol) in N,N-dimethylformamide (50 mL) at 0° was added, portionwise as a solid, dicyclohexylcarbodiimide (1.24 g, 0.006 mol). The reaction mixture was stirred at 0° for 2.5 hours, then at ambient temperature for 72 hours . The solids were filtered and washed with chloroform. The filtrate was concentrated under vacuum and the residue (5.2 g) was chromatographed with 7:3 hexane-ethyl acetate. The resulting solid was triturated with hexane to give the title compound (2.59 g, 0.0044 mol) as a yellow oil. 1H NMR (CDCl3) δ 7.6-7.0(m,11H), 6.8-6.5(m,2H), 3.7(d,2H,J=13.7 Hz), 3.5(t,2H,J=6.4 Hz), 3.4-3.0(m,3 H), 2.9(t,2H,J=6.1 Hz), 1.8-1.1(m,17H), 0 0.9(t,3H,J=6.6 Hz).

Workup

  1. waitat ambient temperature for 72 hours
  2. filtrationThe solids were filtered
  3. washwashed with chloroform
  4. concentrationThe filtrate was concentrated under vacuum
  5. customthe residue (5.2 g) was chromatographed with 7:3 hexane-ethyl acetate
  6. customThe resulting solid was triturated with hexane

Sources & evidence

ORD record
ord-f0ff341b97bc472d819240930b5d06f8
Source dataset
uspto-grants-1994_06
Patent number
US05318984

Reaction notes

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