Dimethylformamide → 2-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridine-7-carbaldehyde

HRID 1394230Notes

Reaction equation

HRID 1394230 reaction equation
Br[C:2]1[C:3]2[N:10]([CH2:11][CH3:12])[C:9]([C:13]3[C:14]([NH2:18])=[N:15][O:16][N:17]=3)=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1.C([Li])CCC.CN(C)[CH:26]=[O:27]>O1CCCC1>[NH2:18][C:14]1[C:13]([C:9]2[N:10]([CH2:11][CH3:12])[C:3]3[C:2]([CH:26]=[O:27])=[CH:7][N:6]=[CH:5][C:4]=3[N:8]=2)=[N:17][O:16][N:15]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 443971924-(7-Bromo-1-ethyl-1H-imidazo[4,5-c]pyridin-2-yl)-1,2,5-oxadiazol-3-amineHCID 178418339Butyllithium

Product 1

HCID 596817552-(4-Amino-furazan-3-yl)-1-ethyl-1H-imidazo[4,5-c]pyridine-7-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of the product from Example 100 (0.1 g, 0.324 mmol) in tetrahydrofuran (4 ml) at −78° C. was treated with a i 0.6M solution of n-butyllithium (0.6 ml, 0.97 mmol) in hexanes. After 5 minutes the mixture was treated with dimethylformamide (0.3 ml) and allowed to reach room temperature. After 30 minutes at room temperature the reaction was carefully quenched with water and extracted into dichloromethane (×2). The organic layer was then washed with brine, dried (Na2SO4) and reduced in vacuo. The residue was purified by silica gel chromatography eluting with ethyl acetate, to afford the title compound, (0.0349, 41%); MS (ES+) m/e 259 [M+H]+.

Workup

  1. customto reach room temperature
  2. customAfter 30 minutes at room temperature the reaction was carefully quenched with water
  3. extractionextracted into dichloromethane (×2)
  4. washThe organic layer was then washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe residue was purified by silica gel chromatography
  7. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-5998436f1af14265b0030e37f58c64e4
Source dataset
uspto-grants-2008_03
Patent number
US07348339B2

Reaction notes

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