Iodoethane → 1-Methyl-1H-pyrazole-3-sulfonic acid benzyl (2-ethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-amide

HRID 1947639Notes

Reaction equation

HRID 1947639 reaction equation
[CH2:1]([N:8]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[NH:23][CH2:22][CH2:21]2)[S:9]([C:12]1[CH:16]=[CH:15][N:14]([CH3:17])[N:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:32][CH3:33]>C1COCC1>[CH2:1]([N:8]([C:18]1[CH:19]=[C:20]2[C:25](=[CH:26][CH:27]=1)[C:24](=[O:28])[N:23]([CH2:32][CH3:33])[CH2:22][CH2:21]2)[S:9]([C:12]1[CH:16]=[CH:15][N:14]([CH3:17])[N:13]=1)(=[O:11])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 672239981-methyl-1H-pyrazole-3-sulfonic acid benzyl-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-amide

Product 1

HCID 498345271-Methyl-1H-pyrazole-3-sulfonic acid benzyl (2-ethyl-1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-amideYield 42.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 1-methyl-1H-pyrazole-3-sulfonic acid benzyl-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-6-yl)-amide (9 mg, 0.022 mmol) and sodium hydride (2 mg of a 60% dispersion in mineral oil, 0.045 mmol) in anhydrous THF (0.5 ml) was added iodoethane (2 μl, 0.045 mmol) and the reaction heated to 110° C. in a microwave for 0.5 hrs. The solvent was evaporated in vacuo and the resulting residue purified by preparative HPLC (Method B) to yield the title compound as a colourless solid (4 mg, 24%). HPLC retention time 4.14 min. Mass spectrum (ES+) m/z 425 (M+H).

Workup

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

Sources & evidence

ORD record
ord-8807bb6f028e4e93a9d8f3f94299bcb5
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

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