6-bromo-N-methylpyridin-2-amine → 6-(4-(2H-benzo[d][1,2,3]triazol-2-yl)but-1-ynyl)-N-methylpyridin-2-amine

HRID 334690Notes

Reaction equation

HRID 334690 reaction equation
Br[C:2]1[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=[CH:4][CH:3]=1.[CH2:10]([N:14]1[N:18]=[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]2=[N:15]1)[CH2:11][C:12]#[CH:13]>>[N:15]1[N:14]([CH2:10][CH2:11][C:12]#[C:13][C:2]2[N:7]=[C:6]([NH:8][CH3:9])[CH:5]=[CH:4][CH:3]=2)[N:18]=[C:17]2[CH:19]=[CH:20][CH:21]=[CH:22][C:16]=12

Participants

3

Reactant 2

HCID 134703156-bromo-N-methylpyridin-2-amineHCID 576917912-but-3-ynyl-2H-benzo[d][1,2,3]triazole

Product 1

HCID 665979666-(4-(2H-benzo[d][1,2,3]triazol-2-yl)but-1-ynyl)-N-methylpyridin-2-amineYield 14.3%

Procedure

The title compound was prepared in accordance with the general method of Example 1, from (6-bromo-pyridin-2-yl)-methyl-amine (105 mg, 0.56 mmol) and 2-but-3-ynyl-2H-benzo[d][1,2,3]triazole (96 mg, 0.56 mmol, Example 109(D)). Reaction time: 3 hours. The crude residue was purified by C18 flash chromatography (water to water/acetonitrile 3:2) to yield 22 mg (80 μmol, 14%) of 6-(4-(2H-benzo[d][1,2,3]triazol-2-yl)but-1-ynyl)-N-methylpyridin-2-amine as a white solid (M.P.=150-154° C.).

Workup

  1. customReaction time
  2. custom3 hours
  3. customThe crude residue was purified by C18 flash chromatography (water to water/acetonitrile 3:2)

Sources & evidence

ORD record
ord-ecfabbd7dfa543aeac20e1fd794fdcba
Source dataset
uspto-grants-2014_11
Patent number
US08883826B2

Reaction notes

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