Azidotrimethylsilane → HCID 178463396, compound

HRID 2193006Notes

Reaction equation

HRID 2193006 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].[N:25]([Si](C)(C)C)=[N+:26]=[N-:27]>CN(C=O)C.CO.O.[Cu]I>[NH:25]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:27]=[N:26]1

Participants

6

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 59375485HCID 59375485, compound

Product 1

HCID 178463396HCID 178463396, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 962WaterSolventHCID 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 (2.0 mL) in a sealed tube. To the solution was added CuI (5.0 mg, 0.020 mmol) and azidotrimethylsilane (270 mg, 2.4 mmol) under an argon atmosphere. The mixture was stirred at 100° C. in a sealed tube for 8 h. The resulting solution was diluted with water (5 mL) and extracted with ethyl acetate (3×5 mL). The combined organic layers were washed with brine (5 mL), dried over magnesium sulfate, filtered, and purified by preparative TLC to afford 9-(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 10.28 (s, 1H), 8.38 (d, J=8.4 Hz, 2H), 8.30 (d, J=6.4 Hz, 1H), 7.38 (d, J=7.2 Hz, 1H), 6.64 (d, J=7.2 Hz, 1H), 4.78 (m, 1H), 1.28 (d, J=6.8 Hz, 3H), 1.04 (s, 9H). LRMS calculated for C20H22N6O [M+H]+, 363; found 363.

Workup

  1. extractionextracted with ethyl acetate (3×5 mL)
  2. washThe combined organic layers were washed with brine (5 mL)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. custompurified by preparative TLC

Sources & evidence

ORD record
ord-e03afd2ba51c463cbc7f9571a39a6b8e
Source dataset
uspto-grants-2012_12
Patent number
US08329722B2

Reaction notes

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