Pyridine → HCID 49834169, compound

HRID 1947634Notes

Reaction equation

HRID 1947634 reaction equation
[CH2:1]([NH:8][C:9]1[CH:18]=[C:17]2[C:12]([CH2:13][CH2:14][NH:15][C:16]2=[O:19])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:26][N:27]1[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[N:28]1.[Cl:36]CCl>>[Cl:36][C:5]1[CH:6]=[CH:7][C:2]([CH2:1][N:8]([C:9]2[CH:18]=[C:17]3[C:12]([CH2:13][CH2:14][NH:15][C:16]3=[O:19])=[CH:11][CH:10]=2)[S:32]([C:29]2[CH:30]=[CH:31][N:27]([CH3:26])[N:28]=2)(=[O:34])=[O:33])=[CH:3][CH:4]=1

Participants

5

Reactant 4

HCID 1049PyridineHCID 6344DichloromethaneHCID 134744661-Methyl-1H-pyrazole-3-sulfonyl chlorideHCID 67223633HCID 67223633, compound

Product 1

HCID 49834169HCID 49834169, compoundYield 41%

Procedure

To a stirred solution of 7-benzylamino-3,4-dihydro-2H-isoquinolin-1-one (100 mg, 0.34 mmol) and pyridine (63 μl, 0.77 mmol) in anhydrous dichloromethane (2 ml) was added 1-methyl-1H-pyrazole-3-sulfonyl chloride (138 mg, 0.77 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 flash column chromatography (50% ethyl acetate in dichloromethane) to afford the title compound as a colourless solid (63 mg, 41%). HPLC retention time 4.16 min. Mass spectrum (ES+) m/z 431 (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 flash column chromatography (50% ethyl acetate in dichloromethane)

Sources & evidence

ORD record
ord-db78560a1666401c8963e98dc7d9e68a
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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