Diisopropylethylamine → HCID 18536489, compound

HRID 412626Notes

Reaction equation

HRID 412626 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH2:21])=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl[CH2:23][C:24]1[N:28]([CH2:29][C:30](=[O:38])[NH:31][CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[C:27]2[CH:39]=[CH:40][C:41]([C:43]#[N:44])=[CH:42][C:26]=2[N:25]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([NH:21][CH2:23][C:24]3[N:28]([CH2:29][C:30](=[O:38])[NH:31][CH:32]4[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]4)[C:27]4[CH:39]=[CH:40][C:41]([C:43]#[N:44])=[CH:42][C:26]=4[N:25]=3)=[CH:17][CH:16]=2)[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 18536348HCID 18536348, compoundHCID 22181157tert-Butyl 4-(4-aminophenoxy)piperidine-1-carboxylate

Product 1

HCID 18536489HCID 18536489, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 4-(4-aminophenoxy)piperidine-1-carboxylic acid tert-butyl ester (8.21 g), 2-chloromethyl-1-(cyclohexylcarbamoylmethyl)-5-cyanobenzimidazole (9.29 g) and diisopropylethylamine (9.8 ml) in dimethylformamide (93 ml) was stirred at 60° C. for 14 hours. After completion of the reaction, the solvent was evaporated and the obtained residue was extracted with ethyl acetate and washed with water. The organic layer was dried over anhydrous magnesium sulfate and the solvent was evaporated. To the obtained residue were added ethyl acetate and hexane and the precipitated solid was collected by filtration, washed with diisopropyl ether and dried under reduced pressure to give the title compound (15.726 g).

Workup

  1. customAfter completion of the reaction
  2. customthe solvent was evaporated
  3. extractionthe obtained residue was extracted with ethyl acetate
  4. washwashed with water
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated
  7. additionTo the obtained residue were added ethyl acetate and hexane
  8. filtrationthe precipitated solid was collected by filtration
  9. washwashed with diisopropyl ether
  10. customdried under reduced pressure

Sources & evidence

ORD record
ord-d2199b703c574100a39c0ea2ae99a299
Source dataset
uspto-grants-2003_05
Patent number
US06562828B1

Reaction notes

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