Benzyl azide → HCID 59375542, compound

HRID 2193007Notes

Reaction equation

HRID 2193007 reaction equation
[C:1]([C:3]1[CH:24]=[CH:23][C:6]2[C:7]([NH:16][CH:17]([CH3:22])[C:18]([CH3:21])([CH3:20])[CH3:19])=[N:8][C:9]3[CH:10]=[CH:11][NH:12][C:13](=[O:15])[C:14]=3[C:5]=2[CH:4]=1)#[CH:2].[CH2:25]([N:32]=[N+:33]=[N-:34])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>CN(C=O)C.CO.[Cu]I>[CH2:25]([N:32]1[CH:2]=[C:1]([C:3]2[CH:24]=[CH:23][C:6]3[C:7]([NH:16][CH:17]([CH3:22])[C:18]([CH3:20])([CH3:19])[CH3:21])=[N:8][C:9]4[CH:10]=[CH:11][NH:12][C:13](=[O:15])[C:14]=4[C:5]=3[CH:4]=2)[N:34]=[N:33]1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 12152Benzyl azideHCID 59375485HCID 59375485, compound

Product 1

HCID 59375542HCID 59375542, compound

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 21901440N,N-dimethylformamide methanolSolvent

Conditions

Temperature
100 °C

Procedure

9-ethynyl-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one (150 mg, 0.47 mmol) was dissolved in DMF/MeOH (2 mL) in a sealed tube. To the solution was added CuI (5.0 mg, 0.020 mmol) and Bn—N3 (310 mg, 2.4 mmol) under an argon atmosphere. The mixture was stirred at 100° C. for 8 h, then the resulting solution was filtered and purified by reverse phase HPLC to afford 9-(1-benzyl-1H-1,2,3-triazol-4-yl)-6-[(1,2,2-trimethylpropyl)amino]benzo[c]-1,6-naphthyridin-1(2H)-one. 1H NMR (400 MHz, MeOD) δ 10.30 (s, 1H), 8.64 (m, 2H), 8.30 (d, J=8.4 Hz, 1H), 7.65 (d, J=6.8 Hz, 1H), 7.40 (m, 5H), 6.93 (d, J=7.2 Hz, 1H), 5.70 (s, 2H), 4.46 (m, 1H), 1.46 (d, J=6.8 Hz, 3H), 1.09 (s, 9H). LRMS calculated for C27H28N6O [M+H]+, 453; found 454.

Workup

  1. filtrationthe resulting solution was filtered
  2. custompurified by reverse phase HPLC

Sources & evidence

ORD record
ord-87a56db9e11640899de73fd151738054
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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