Diisopropylethylamine → HCID 17836468, compound

HRID 348515Notes

Reaction equation

HRID 348515 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][CH2:7][S:8][C:9]1[NH:10][C:11]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH3:2].C(N(C(C)C)CC)(C)C.[CH3:30][C:31]1[C:39]2[C:38]([CH2:40]Br)=[CH:37][S:36][C:35]=2[CH:34]=[CH:33][CH:32]=1.C(=O)(O)[O-].[Na+]>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][CH2:7][S:8][C:9]1[N:13]([CH2:40][C:38]2[C:39]3[C:31]([CH3:30])=[CH:32][CH:33]=[CH:34][C:35]=3[S:36][CH:37]=2)[C:12]2[CH:14]=[CH:15][C:16]([O:18][CH3:19])=[CH:17][C:11]=2[N:10]=1)[CH3:2].[CH2:1]([O:3][C:4](=[O:20])[CH2:5][CH2:6][CH2:7][S:8][C:9]1[N:10]([CH2:40][C:38]2[C:39]3[C:31]([CH3:30])=[CH:32][CH:33]=[CH:34][C:35]=3[S:36][CH:37]=2)[C:11]2[CH:17]=[C:16]([O:18][CH3:19])[CH:15]=[CH:14][C:12]=2[N:13]=1)[CH3:2]

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 516892Sodium BicarbonateHCID 9813529HCID 9813529, compoundHCID 17836477HCID 17836477, compound

Product 2

HCID 17836468HCID 17836468, compoundYield 17%HCID 17836475HCID 17836475, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

539 mg (1.44 mmol) of 4-(5-methoxybenzimidazole-2-ylthio)butanoate ethyl ester were suspended in 4 ml of toluene followed by the addition of 616 μl (3.60 mmol) of diisopropylethylamine and 384 mg (1.59 mmol) of 4-methyl-3-(bromomethyl)benzo[b]thiophene and heating at 100° C. After allowing to react overnight, saturated sodium bicarbonate solution was added followed by extraction with ethyl acetate. The organic phase was washed with water followed by drying with magnesium sulfate and concentrating the solvent under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to obtain 114 mg of 4-(1-((4-methylbenzothiophene-3-yl)methyl)-5-methoxybenzimidazole-2-ylthio)butanoate ethyl ester (yield: 17%) and 68 mg of 4-(1-((4-methylbenzothiophene-3-yl)methyl)-6-methoxybenzimidazole-2-ylthio)butanoate ethyl ester (yield: 10%).

Workup

  1. customto react overnight
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe organic phase was washed with water
  4. dry with materialby drying with magnesium sulfate
  5. concentrationconcentrating the solvent under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-486c3bfecb664a3c9241678f78ef23ab
Source dataset
uspto-grants-2007_02
Patent number
US07176320B2

Reaction notes

Loading…