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

HRID 374070Notes

Reaction equation

HRID 374070 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) δ7.6-7.0(m,11H), 6.8-6.5(m,2H), 3.7(d,2H,J=13.7Hz), 3.5(t,2H,J=6.4Hz), 3.4-3.0(m,3H), 2.9(t,2 H,J=6.1Hz), 1.8-1.1(m,17H), 0.9(t,3H,J=6.6Hz).

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-b98fcec9a84f4e43a3a0a829780bd58b
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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