Pyridine → 1-Methyl-1H-imidazole-4-sulfonic acid (4-chloro-benzyl)-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-7-yl)-amide

HRID 1947648Notes

Reaction equation

HRID 1947648 reaction equation
[Cl:1][C:2]1[CH:22]=[CH:21][C:5]([CH2:6][NH:7][C:8]2[CH:17]=[C:16]3[C:11]([C:12]([CH3:20])([CH3:19])[CH2:13][NH:14][C:15]3=[O:18])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:29][N:30]1[CH:34]=[C:33]([S:35](Cl)(=[O:37])=[O:36])[N:32]=[CH:31]1>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([C:8]2[CH:17]=[C:16]3[C:11]([C:12]([CH3:19])([CH3:20])[CH2:13][NH:14][C:15]3=[O:18])=[CH:10][CH:9]=2)[S:35]([C:33]2[N:32]=[CH:31][N:30]([CH3:29])[CH:34]=2)(=[O:37])=[O:36])=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 27368871-methyl-1H-imidazole-4-sulfonyl chlorideHCID 67224204HCID 67224204, compound

Product 1

HCID 498345291-Methyl-1H-imidazole-4-sulfonic acid (4-chloro-benzyl)-(4,4-dimethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-7-yl)-amideYield 54.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
150 °C

Procedure

To a stirred solution of 7-(4-chloro-benzylamino)-4,4-dimethyl-3,4-dihydro-2H-isoquinolin-1-one (20 mg, 0.06 mmol) and pyridine (12 μl, 0.14 mmol) in anhydrous acetonitrile (1 ml) was added 1-methyl-1H-imidazole-4-sulfonyl chloride (25 mg, 0.14 mmol) and the reaction heated to 150° C. in a microwave for 0.5 hrs. The solvent was evaporated in vacuo and the crude residue purified by preparative HPLC (Method A) to afford the title compound as a colourless solid (15 mg, 21%). HPLC retention time 4.07 min. Mass spectrum (ES+) m/z 459 (M+H).

Workup

  1. customThe solvent was evaporated in vacuo
  2. customthe crude residue purified by preparative HPLC (Method A)

Sources & evidence

ORD record
ord-2dc0cf9e31494cae9a961ac3e95c8bd5
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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