Water → N-[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethyl]-3-vinyl-5-nitrobenzamide

HRID 2390064Notes

Reaction equation

HRID 2390064 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][CH2:13][NH2:14])[CH:6]([CH2:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)[CH2:5]2.[CH:23]([C:25]1[CH:26]=[C:27]([CH:31]=[C:32]([N+:34]([O-:36])=[O:35])[CH:33]=1)[C:28](O)=[O:29])=[CH2:24].CCN=C=NCCCN(C)C.O>C(Cl)(Cl)Cl>[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH2:8][N:7]([CH2:12][CH2:13][NH:14][C:28](=[O:29])[C:27]1[CH:31]=[C:32]([N+:34]([O-:36])=[O:35])[CH:33]=[C:25]([CH:23]=[CH2:24])[CH:26]=1)[CH:6]([CH2:15][C:16]1[CH:17]=[CH:18][C:19]([F:22])=[CH:20][CH:21]=1)[CH2:5]2

Participants

6

Reactant 4

HCID 962WaterHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 184293443-Vinyl-5-nitrobenzoic acidHCID 593230712-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine

Product 1

HCID 59323053N-[2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethyl]-3-vinyl-5-nitrobenzamideYield 74%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

100 mg of 2-[6-fluoro-3-(4-fluorobenzyl)-3,4-dihydroisoquinolin-2(1H)-yl]ethanamine obtained in Example 120-b) and 65 mg of 3-vinyl-5-nitrobenzoic acid were dissolved in 1 mL of chloroform, and 96 mg of WSC was added thereto, followed by stirring for 30 minutes. After completion of the reaction, water was added to the reaction liquid, followed by extraction with ethyl acetate, and the organic layer was then washed with an aqueous sodium bicarbonate solution and saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue obtained was purified using silica gel chromatography (chloroform:methanol=10:1) to obtain 112 mg (yield 74%) of a title compound as a yellow solidified product.

Workup

  1. additionwas added to the reaction liquid
  2. extractionfollowed by extraction with ethyl acetate
  3. washthe organic layer was then washed with an aqueous sodium bicarbonate solution and 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-f4b5dd0389e84658aacc8cecb59332ef
Source dataset
uspto-grants-2012_09
Patent number
US08273766B2

Reaction notes

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