1-(Azidomethyl)-4-methoxybenzene → 12-Methyl-5-(4-methoxybenzyl)-3,4,5,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-diene

HRID 2354897Notes

Reaction equation

HRID 2354897 reaction equation
[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[CH2:4][C:5](N1CCCC1)=[CH:6]2.[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([CH2:22][N:23]=[N+:24]=[N-:25])=[CH:20][CH:19]=1>>[CH3:1][N:2]1[CH:7]2[CH2:8][CH2:9][CH2:10][CH:3]1[C:4]1[N:25]=[N:24][N:23]([CH2:22][C:21]3[CH:20]=[CH:19][C:18]([O:17][CH3:16])=[CH:27][CH:26]=3)[C:5]=1[CH2:6]2

Participants

3

Reactant 2

HCID 109317671-(Azidomethyl)-4-methoxybenzeneHCID 596794649-Methyl-3-(pyrrolidin-1-yl)-9-azabicyclo[3.3.1]non-3-ene

Product 1

HCID 5967949812-Methyl-5-(4-methoxybenzyl)-3,4,5,12-tetraaza-tricyclo[6.3.1.02,6]dodeca-2(6),3-dieneYield 57.6%

Conditions

Temperature
50 °C

Procedure

A mixture of 9-methyl-3-(pyrrolidin-1-yl)-9-azabicyclo[3.3.1]non-3-ene (1.2 g, 5.9 mmol) and 4-methoxybenzylazide (0.96 g, 5.9 mmol) was heated at 50° C. for 2 days. The crude mixture was purified by prep HPLC to afford the product (1.0 g, 3.4 mmol, 57% yield) as yellow oil.

Workup

  1. customThe crude mixture was purified by prep HPLC

Sources & evidence

ORD record
ord-725da804052b42e7b859675e18965757
Source dataset
uspto-grants-2010_07
Patent number
US07754712B2

Reaction notes

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