Benzyl azide → HCID 44200196, compound

HRID 547469Notes

Reaction equation

HRID 547469 reaction equation
[C:1]([C:3]1[N:4]=[C:5]2[C:11]([C:12](=[O:17])[C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:10][NH:9][C:6]2=[N:7][CH:8]=1)#[CH:2].[CH2:18]([N:25]=[N+:26]=[N-:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O=C1O[C@H]([C@H](CO)O)C(O)=C1O>C(O)(C)(C)C.O.[O-]S([O-])(=O)=O.[Cu+2]>[CH2:18]([N:25]1[CH:2]=[C:1]([C:3]2[N:4]=[C:5]3[C:11]([C:12](=[O:17])[C:13]([CH3:14])([CH3:16])[CH3:15])=[CH:10][NH:9][C:6]3=[N:7][CH:8]=2)[N:27]=[N:26]1)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 3

HCID 12152Benzyl azideHCID 44199847HCID 44199847, compoundHCID 54670067L-Ascorbic Acid

Product 1

HCID 44200196HCID 44200196, compoundYield 23%

Reagents, catalysts & solvents 3

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent2×HCID 6386tert-ButanolSolvent

Procedure

A solution of 1-(2-ethynyl-5H-pyrrolo[2,3-b]pyrazin-7-yl)-2,2-dimethyl-propan-1-one (0.100 g, 0.44 mmol), benzyl azide (0.055 mL, 0.44 mmol), CuSO4 (0.007 g, 0.04 mmol), and L-ascorbic acid (0.078 g, 0.44 mmol) in 3 mL of tert-butanol and 3 mL of water was stirred for 1.5 h, then diluted with 30 mL of water and extracted with 100 mL of ethyl acetate. The organic layer was dried over MgSO4, filtered and concentrated to a residue. Silica gel chromatography (0->50% EtOAc/hexanes) afforded 0.036 g (23%) of 1-[2-(1-benzyl-1H-[1,2,3]triazol-4-yl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as an off-white solid. MS: 361 M+1, M.P. 235.0-237.0° C.

Workup

  1. extractionextracted with 100 mL of ethyl acetate
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to a residue

Sources & evidence

ORD record
ord-3beb4f89a1b74f18bcf622cb8522b8d4
Source dataset
uspto-grants-2011_05
Patent number
US07939531B2

Reaction notes

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