Azidotrimethylsilane → HCID 178424698, compound

HRID 1826708Notes

Reaction equation

HRID 1826708 reaction equation
[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([C:13]#[C:14][C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=3)[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2].[N:22]([Si](C)(C)C)=[N+:23]=[N-:24]>CN(C=O)C>[CH:1]([C:4]1[N:8]2[CH:9]=[C:10]([C:13]3[N:22]=[N:23][NH:24][C:14]=3[C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([CH3:21])[N:16]=3)[CH:11]=[CH:12][C:7]2=[N:6][N:5]=1)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 78378AzidotrimethylsilaneHCID 22136204HCID 22136204, compound

Product 1

HCID 178424698HCID 178424698, compoundYield 39.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 10 mL flask was added 100 mg (0.36 mmol) of 3-Isopropyl-6-(6-methylpyridin-2-ylethynyl)-[1,2,4]triazolo(4,3-a)pyridine, 1.5 mL of anhydrous DMF, and 168 μL (1.3 mmol) of azidotrimethylsilane. The reaction mixture was heated to reflux for 16 hours. After concentrating, the residue was suspended in 30 mL of water and was extracted with (2×30 mL) ethyl acetate. The organic extracts were combined, washed with 20 mL of water, 20 mL of brine, dried over magnesium sulfate, filtered, and concentrated. Product was purified by Shimodzu prep. HPLC using a 5 to 60% acetonitrile/buffer gradient (buffer is water with 0.1% formic acid, and the acetonitrile contains 0.1% formic acid as well) which yielded 45 milligrams (39%) of a light brown solid. HPLC tR=3.71 min (98%), LC-MS=320 (M+1).

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 16 hours
  3. concentrationAfter concentrating
  4. extractionwas extracted with (2×30 mL) ethyl acetate
  5. washwashed with 20 mL of water, 20 mL of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customProduct was purified by Shimodzu prep

Sources & evidence

ORD record
ord-49f7286a5905494fb15e1d42eebf8e77
Source dataset
uspto-grants-2006_05
Patent number
US07053095B2

Reaction notes

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