Ethanol → 2-(1-Methyl-3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)ethanamine

HRID 1621102Notes

Reaction equation

HRID 1621102 reaction equation
[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][N:9]2C(=O)C3C(=CC=CC=3)C2=O)=[N:5][C:4]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[N:3]1.CCO>CN>[CH3:1][N:2]1[C:6]([CH2:7][CH2:8][NH2:9])=[N:5][C:4]([C:20]2[CH:25]=[CH:24][N:23]=[CH:22][CH:21]=2)=[N:3]1

Participants

4

Reactant 2

HCID 702Ethanol2×HCID 712792712-(2-(1-Methyl-3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)isoindoline-1,3-dione

Product 1

HCID 712792862-(1-Methyl-3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)ethanamineYield 74.2%

Reagents, catalysts & solvents 1

HCID 6329MethylamineSolvent2×

Procedure

2-(2-(1-Methyl-3-(pyridin-4-yl)-1H-1,2,4-triazol-5-yl)ethyl)isoindoline-1,3-dione (114.9 mg, 345 μmol) was dissolved in methylamine solution in EtOH (3.07 mL, 22.5 mmol) and stirred at RT for 1 h. The reaction mixture was evaporated to give light brown solid. The solid was again dissolved in methylamine solution in EtOH (3.07 mL, 22.5 mmol) and the mixture was heated to 50° C. and stirred for 3 h. All volatiles were removed in vacuo and the residue was suspended in dichloromethane (1.5 mL) and filtered. The filtrate was evaporated to give the product as light yellow solid (81.3 mg (80% purity), 256 μmol, 74.2%) which was used without purification for the next step. MS: M=204.2 (M+H)+

Workup

  1. customThe reaction mixture was evaporated
  2. customto give light brown solid
  3. temperaturethe mixture was heated to 50° C.
  4. stirringstirred for 3 h
  5. customAll volatiles were removed in vacuo
  6. filtrationfiltered
  7. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-2aa591603db545b990db7cbae8398156
Source dataset
uspto-grants-2014_07
Patent number
US08772510B2

Reaction notes

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