Dimethyl Sulfoxide → [3-(2-Quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophene-2-carboxamide

HRID 2248908Notes

Reaction equation

HRID 2248908 reaction equation
C[C:2]1[C:3]2[CH:13]=[C:12]([O:14][CH2:15][C:16]3[CH:21]=[CH:20][CH:19]=[C:18]([O:22][CH2:23][C:24]4[CH:33]=[CH:32][C:31]5[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=5)[N:25]=4)[CH:17]=3)[CH:11]=[CH:10][C:4]=2SC=1C(O)=O.C(N(CC)CC)C.[OH2:41].N[C:43]1[NH:47]N=NN=1.[CH3:48][S:49]([CH3:51])=O>>[N:25]1[C:26]2[C:31](=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:32]=[CH:33][C:24]=1[CH2:23][O:22][C:18]1[CH:17]=[C:16]([CH:21]=[CH:20][CH:19]=1)[CH2:15][O:14][C:12]1[C:13]2[C:3]([CH3:2])=[C:51]([C:43]([NH2:47])=[O:41])[S:49][C:48]=2[CH:4]=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 149952903-Methyl 5-[3(2-quinolinylmethyloxy)-benzyloxy]benzo(b)thiophene-2-carboxylic acidHCID 178509300HCID 178509300, compound

Product 1

HCID 86745011[3-(2-Quinolinylmethyloxy)benzyloxy]-3-methylbenzo(b)thiophene-2-carboxamide

Conditions

Temperature
60 °C

Procedure

To a stirred solution of 3-methyl-5-[3-(2-quinolinylmethyloxy)benzyloxy]benzo(b)thiophene-2-carboxylic acid (250 mg, 0.55 mmol) in DMSO (6 ml) at room temperature is added 1,1'-carboxyldiimidazole (178 mg, 1.10 mmol) and the resulting solution is stirred at 60° C. for 1 hour. Triethylamine (153 μL, 1.10 mmol) and 5-aminotetrazole monohydrate (113.2 mg, 1.10 mmol) are added successively and the solution stirred at 60° C. for 16 hours. The reaction mixture is cooled to room temperature and poured over ice-water. The pH is adjusted to 10 and the aqueous layer washed with ether. The pH is then adjusted to 3 and the precipitated material obtained by filtration and washing successively with water, ethanol and methylene chloride. Further drying under vacuum affords N-1H-(5-tetrazolyl)-5-[3-(2-quinolinylmethyloxy)benzyloxy ]-3-methylbenzo(b)thiophene-2-carboxamide (M.P. 220-224° C. (dec)).

Workup

  1. stirringthe solution stirred at 60° C. for 16 hours
  2. temperatureThe reaction mixture is cooled to room temperature
  3. washthe aqueous layer washed with ether
  4. customthe precipitated material obtained by filtration
  5. washwashing successively with water, ethanol and methylene chloride
  6. customFurther drying under vacuum

Sources & evidence

ORD record
ord-9b37c054f2a6481b9e801d9161fea508
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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