Trifluoroacetic acid → cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide

HRID 43975Notes

Reaction equation

HRID 43975 reaction equation
ClC1N=C(C(N[C@H]2CCN(C3N=NN(CC4C=CC(OC)=CC=4)N=3)C[C@H]2OC)=O)NC=1CC.[Cl:34][C:35]1[N:36]=[C:37]([C:42]([NH:44][C@H:45]2[CH2:50][CH2:49][N:48]([C:51]([C:53]3[N:54]=[N:55][NH:56][N:57]=3)=[O:52])[CH2:47][C@H:46]2[O:58][CH3:59])=[O:43])[NH:38][C:39]=1[CH2:40][CH3:41].FC(F)(F)C(O)=O>C1(OC)C=CC=CC=1>[Cl:34][C:35]1[N:36]=[C:37]([C:42]([NH:44][C@H:45]2[CH2:50][CH2:49][N:48]([C:51]([C:53]3[N:54]=[N:55][NH:56][N:57]=3)=[O:52])[CH2:47][C@H:46]2[O:58][CH3:59])=[O:43])[NH:38][C:39]=1[CH2:40][CH3:41]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86762084cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(4-methoxybenzyl)-2H-tetrazol-5-yl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide

Product 1

HCID 86762083cis(+/-)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amideYield 21.4%

Reagents, catalysts & solvents 1

HCID 7519AnisoleSolvent

Conditions

Temperature
45 °C

Procedure

cis(±)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(2H-tetrazol-5-yl)carbonyl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide cis(±)-4-Chloro-5-ethyl-N-{3-methoxy-1-[(4-methoxybenzyl)-2H-tetrazol-5-yl]piperidin-4-yl}-1H-imidazole-2-carboxylic acid amide obtained in Example (260a) (28 mg, 0.05 mmol) was dissolved in anisole (1 mL). Trifluoroacetic acid (2 mL) was added, and the mixture was stirred at 45° C. for 3.5 hours. Following concentration under reduced pressure, the reaction solution was diluted and extracted with dichloromethane and aqueous sodium bicarbonate solution. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under reduced pressure. The residue was solidified by adding chloroform and hexane to obtain 4.1 mg of the title compound as a white solid (20%).

Workup

  1. concentrationconcentration under reduced pressure
  2. additionthe reaction solution was diluted
  3. extractionextracted with dichloromethane and aqueous sodium bicarbonate solution
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. additionby adding chloroform and hexane

Sources & evidence

ORD record
ord-0b4693a0466b433bacb635cee146a4db
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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