1-Hydroxybenzotriazole → N-(2-Methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-5-bromo-2,4-dimethoxybenzamide

HRID 1872723Notes

Reaction equation

HRID 1872723 reaction equation
[Br:1][C:2]1[C:3]([O:13][CH3:14])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.ON1C2C=CC=CC=2N=N1.[NH2:25][C:26]1[CH:35]=[CH:34][CH:33]=[C:32]2[C:27]=1[CH2:28][CH2:29][N:30]([CH3:36])[CH2:31]2>CN(C=O)C>[CH3:36][N:30]1[CH2:29][CH2:28][C:27]2[C:32](=[CH:33][CH:34]=[CH:35][C:26]=2[NH:25][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Br:1])[C:3]([O:13][CH3:14])=[CH:4][C:5]=2[O:11][CH3:12])[CH2:31]1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 135050975-Bromo-2,4-dimethoxybenzoic acidHCID 141712692-Methyl-1,2,3,4-tetrahydroisoquinolin-5-amine

Product 1

HCID 18687427N-(2-Methyl-1,2,3,4-tetrahydroisoquinolin-5-yl)-5-bromo-2,4-dimethoxybenzamideYield 27.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2,4-dimethoxybenzoic acid (0.296 g, 1.1 mmol), 1-(3-dimethyl aminopropyl)-3-ethylcarbodiimide hydrochloride (0.186 g, 0.94 mmol) and 1-hydroxybenzotriazole (0.144 g, 0.94 mmol) were dissolved in dry DMF (10 ml) and stirred at room temperature under argon for 25 mins before 5-amino-2-methyl-1,2,3,4-tetrahydroisoquinoline (0.153 g, 0.94 mmol) was added. The mixture was then stirred overnight under argon at room temperature. The DMF was removed in vacuo and the residue taken up into ethyl acethate and washed with water. The organic layer was dried over magnesium sulfate, concentrated in vacuo and the residue recrystallised from ethyl acethate/hexane to afford the title compound as a solid (0.106 g)

Workup

  1. additionwas added
  2. customThe DMF was removed in vacuo
  3. washwashed with water
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customthe residue recrystallised from ethyl acethate/hexane

Sources & evidence

ORD record
ord-38f0ed8286064611a65f3d7e89276024
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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