Iodoethane → HCID 49834168, compound

HRID 1947635Notes

Reaction equation

HRID 1947635 reaction equation
[Cl:1][C:2]1[CH:29]=[CH:28][C:5]([CH2:6][N:7]([C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][NH:23][C:24]3=[O:27])=[CH:19][CH:18]=2)[S:8]([C:11]2[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].I[CH2:33][CH3:34]>C1COCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][N:7]([C:17]2[CH:26]=[C:25]3[C:20]([CH2:21][CH2:22][N:23]([CH2:33][CH3:34])[C:24]3=[O:27])=[CH:19][CH:18]=2)[S:8]([C:11]2[CH:15]=[CH:14][N:13]([CH3:16])[N:12]=2)(=[O:9])=[O:10])=[CH:28][CH:29]=1

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 49834169HCID 49834169, compound

Product 1

HCID 49834168HCID 49834168, compoundYield 24%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
110 °C

Procedure

To a suspension of 1-methyl-1H-pyrazole-3-sulfonic acid (4-chloro-benzyl)-(1-oxo-1,2,3,4-tetrahydro-isoquinolin-7-yl)-amide (20 mg, 0.046 mmol) and sodium hydride (3 mg, 0.055 mmol) in anhydrous THF (1 ml) was added iodoethane (8 μl, 0.055 mmol) and the reaction heated to 110° C. in a microwave for 0.5 h. 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 (5 mg, 24%). HPLC retention time 4.34 min. Mass spectrum (ES+) m/z 459 (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-7666fb25fc664d5fb2cc4c8d7819b121
Source dataset
uspto-grants-2013_03
Patent number
US08399481B2

Reaction notes

Loading…