1-Hydroxybenzotriazole → HCID 18687383, compound

HRID 1872730Notes

Reaction equation

HRID 1872730 reaction equation
[Br:1][C:2]1[C:3]([CH3:13])=[CH:4][C:5]([O:11][CH3:12])=[C:6]([CH:10]=1)[C:7]([OH:9])=O.ON1C2C=CC=CC=2N=N1.[NH2:24][C:25]1[CH:34]=[CH:33][CH:32]=[C:31]2[C:26]=1[CH2:27][CH2:28][N:29]([CH3:35])[CH2:30]2>CN(C=O)C>[CH3:35][N:29]1[CH2:28][CH2:27][C:26]2[C:31](=[CH:32][CH:33]=[CH:34][C:25]=2[NH:24][C:7](=[O:9])[C:6]2[CH:10]=[C:2]([Br:1])[C:3]([CH3:13])=[CH:4][C:5]=2[O:11][CH3:12])[CH2:30]1

Participants

5

Reactant 3

HCID 757711-HydroxybenzotriazoleHCID 141712692-Methyl-1,2,3,4-tetrahydroisoquinolin-5-amineHCID 186873935-Bromo-2-methoxy-4-methylbenzoic acid

Product 1

HCID 18687383HCID 18687383, compoundYield 53.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

5-Bromo-2-methoxy-4-methylbenzoic acid (0.245 g, 1 mmol), 1-(3-dimethyl-aminopropyl)-3-ethylcarbodiimide hydrochloride (0.200 g, 1 mmol) and 1-hydroxy-benzotriazole (0.155 g, 1 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 (0.163 g, 1 mmol) was added. The mixture was then stirred for 24 under argon at room temperature. The DMF was removed in vacuo and the residue suspended in ethyl acethate and washed with water. The insoluble white precipithate was filtered off, washed with water then dried to afford the title compound (210 mg).

Workup

  1. additionwas added
  2. customThe DMF was removed in vacuo
  3. washwashed with water
  4. filtrationThe insoluble white precipithate was filtered off
  5. washwashed with water
  6. customthen dried

Sources & evidence

ORD record
ord-0b93a15b78674009996c94ea6318d190
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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