Acetic Anhydride → HCID 68776251, compound

HRID 241019Notes

Reaction equation

HRID 241019 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([NH2:11])[N:10]=[C:4]2[CH:3]=1.C(N(C(C)C)CC)(C)C.[C:21](OC(=O)C)(=[O:23])[CH3:22]>CN(C1C=CN=CC=1)C.C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[N:8]=[C:9]([NH:11][C:21](=[O:23])[CH3:22])[N:10]=[C:4]2[CH:3]=1

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 81531DiisopropylethylamineHCID 545940257-Bromo[1,2,4]triazolo[1,5-a]pyridin-2-amine

Product 1

HCID 68776251HCID 68776251, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 7-Bromo-[1,2,4]triazolo[1,5-a]pyridin-2-ylamine (prepared using the procedure in WO2006038116) (0.150 g, 0.704 mmol), diisopropylethylamine (0.363 g, 2.81 mmol), catalytic DMAP (0.09 g, 0.07 mmol) in anhydrous THF (4 mL) was added acetic anhydride (0.216 g, 2.11 mmol). The reaction mixture was stirred at 50° C. for 22 h under N2 (g). After cooling to room temperature the mixture was concentrated, diluted with ethyl acetate (50 mL), washed with saturated sodium bicarbonate (40 mL), brine (40 mL), and dried over anhydrous sodium sulfate. Filtration and concentration followed by column chromatography of the residue on silica (95:5 dichlormethane/methanol) afforded N-(7-bromo-[1,2,4]triazolo[1,5-a]pyridin-2-yl)acetamide (0.170 g, 95% yield) as a brown oil. MS (EI) for C8H7BrN4O: 256 (MH+).

Workup

  1. temperatureAfter cooling to room temperature the mixture
  2. concentrationwas concentrated
  3. additiondiluted with ethyl acetate (50 mL)
  4. washwashed with saturated sodium bicarbonate (40 mL), brine (40 mL)
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-fe1dd199ee6c4c64bbdfc8755d6b987e
Source dataset
uspto-grants-2014_02
Patent number
US08648066B2

Reaction notes

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