Water → HCID 10432968, compound

HRID 374066Notes

Reaction equation

HRID 374066 reaction equation
[C:1]1([C:7]2[N:8]=[C:9]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH2:24])[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(N(CC)CC)C.[C:32](Cl)(=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38].O>C(Cl)Cl>[C:1]1([C:7]2[N:8]=[C:9]([NH:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:32](=[O:39])[CH2:33][CH2:34][CH2:35][CH2:36][CH2:37][CH3:38])[NH:10][C:11]=2[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 17313Heptanoyl chlorideHCID 10403746HCID 10403746, compound

Product 1

HCID 10432968HCID 10432968, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Part B. To a solution of 5-(4,5-diphenyl-1H-imidazol-2-ylamino)-aminopentane (1.7 g, 0.00531 mol) and triethylamine (0.58 g, 0.0058 mol) in methylene chloride cooled to 0° under a nitrogen atmosphere, heptanoyl chloride (0.788 g, 0.00531 mol) was added slowly. The reaction mixture was stirred for 1 hour at 0°, poured into water and extracted with methylene chloride (2×50 mL). The combined organic extract was washed with water, brine, dried over magnesium sulfate and concentrated to give N-[5-(4,5-diphenyl-1H-imidazol-2-ylamino)pentyl]heptanamide as a viscous oil. The product was purified by flash chromatography on silica gel (250 mL) eluting methylene chloride:methanol (95:5 v:v), to give an amber foam (1.3 g, 0.003 mol). 1H NMR (CDCl3) δ7.43-7.15(m,10H), 6.3(m,1H), 3.24-3.1(m,4H), 2.09(t,2H), 1.6-1.16(m,14H), 0.84(t,3H).

Workup

  1. extractionextracted with methylene chloride (2×50 mL)
  2. extractionThe combined organic extract
  3. washwas washed with water, brine
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-f6ffa23bd85c42c49ee8b0c104a44f32
Source dataset
uspto-grants-1992_11
Patent number
US05166214

Reaction notes

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