Water → HCID 59323200, compound

HRID 2390071Notes

Reaction equation

HRID 2390071 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:30]=[CH:31][CH:32]=1)[CH2:7][NH:8][CH2:9][CH2:10][N:11]1[CH:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH2:12]1)([O-:3])=[O:2].Br[CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36].C(=O)([O-])[O-].[K+].[K+].O>C(#N)C>[CH2:38]([O:37][C:35](=[O:36])[CH2:34][N:8]([CH2:7][C:6]1[CH:30]=[CH:31][CH:32]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)[CH2:9][CH2:10][N:11]1[CH:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([F:28])=[CH:24][CH:23]=2)[CH2:19][C:18]2[C:13](=[CH:14][CH:15]=[C:16]([F:29])[CH:17]=2)[CH2:12]1)[CH3:39]

Participants

6

Reactant 4

HCID 962WaterHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 59323468HCID 59323468, compound

Product 1

HCID 59323200HCID 59323200, compoundYield 77.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

106 mg of N-(3-nitrobenzyl)-2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine obtained in Example 123-b), 40 mg of ethyl bromoacetate, and 33 mg of potassium carbonate were dissolved in 1 mL of acetonitrile, followed by stirring at room temperature for 3 hours. After completion of the reaction, water was added to the reaction liquid, followed by extraction with chloroform. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using PLC (chloroform:methanol=20:1) to obtain 97 mg (yield 76%) of a title compound as a pale yellow oily substance.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue obtained
  7. customwas purified

Sources & evidence

ORD record
ord-81fce6efcf124146b83b82c527d06e31
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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