Pyridine → HCID 49834525, compound

HRID 1947652Notes

Reaction equation

HRID 1947652 reaction equation
[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][NH:7][C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([CH:18]([CH3:20])[CH3:19])[C:11]3=[O:21])=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:30][N:31]1[CH:35]=[C:34]([S:36](Cl)(=[O:38])=[O:37])[N:33]=[CH:32]1>ClCCl>[Cl:1][C:2]1[CH:23]=[CH:22][C:5]([CH2:6][N:7]([C:8]2[CH:9]=[C:10]3[C:14](=[CH:15][CH:16]=2)[C:13](=[O:17])[N:12]([CH:18]([CH3:20])[CH3:19])[C:11]3=[O:21])[S:36]([C:34]2[N:33]=[CH:32][N:31]([CH3:30])[CH:35]=2)(=[O:38])=[O:37])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 67223522HCID 67223522, compound

Product 1

HCID 49834525HCID 49834525, compoundYield 7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 5-(4-chloro-benzylamino)-2-isopropyl-isoindole-1,3-dione (50 mg, 0.15 mmol) and pyridine (36 μl, 0.45 mmol) in anhydrous dichloromethane (2 ml) was added 1-methyl-1H-imidazole-4-sulphonyl chloride (60 mg, 0.27 mmol) and the reaction heated at reflux for 15 hrs. The reaction was cooled and the solvent evaporated in vacuo. The crude residue was purified by preparative HPLC (Method D) to afford the title compound as a colourless solid (5 mg, 7%). HPLC retention time 8.14 min. Mass spectrum (ES+) m/z 473 (M+H).

Workup

  1. temperaturethe reaction heated
  2. temperatureat reflux for 15 hrs
  3. temperatureThe reaction was cooled
  4. customthe solvent evaporated in vacuo
  5. customThe crude residue was purified by preparative HPLC (Method D)

Sources & evidence

ORD record
ord-13fb84ee3a834f05b1d5a78e934b2021
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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