Hydrazine → HCID 178474032, compound

HRID 537065Notes

Reaction equation

HRID 537065 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:15][C:14]([Br:16])=[C:13]([C:17]([NH2:19])=O)[CH:12]=2)[C:8]([CH3:20])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C[N:22]([CH:24](OC)OC)C.[NH2:29]N>C1(C)C=CC=CC=1>[Br:16][C:14]1[O:15][C:11]([C:9]2[C:8]([CH3:20])=[CH:7][N:6]=[C:5]([NH:4][C:1](=[O:3])[CH3:2])[CH:10]=2)=[CH:12][C:13]=1[C:17]1[N:22]=[CH:24][NH:29][N:19]=1

Participants

5

Reactant 3

HCID 9321HydrazineHCID 78373Dimethylformamide dimethyl acetalHCID 667482995-(2-Acetamido-5-methylpyridin-4-yl)-2-bromo-3-furamide

Product 1

HCID 178474032HCID 178474032, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

To a suspension of 5-(2-acetamido-5-methylpyridin-4-yl)-2-bromo-3-furamide (8.5 g, 25.2 mmol) in dry toluene (260 mL) was added DMF-DMA (8.85 g, 74.0 mmol). The reaction mixture was allowed to stir at 50° C. overnight and then concentrated. The residue was resuspended in AcOH (90 mL) and hydrazine (3.77 g, 117.6 mmol) was added dropwise at rt. The reaction mixture was allowed to stir for 2 h and then concentrated. The mixture was azeotroped several times with toluene and then the residue was suspended in EtOAc and water. The mixture was basified with saturated aqueous NaHCO3 to pH=8.5. The mixture was filtered and the solid was dried to give N-{4-[5-bromo-4-(1H-1,2,4-triazol-3-yl)-2-furyl]-5-methylpyridin-2-yl}acetamide (6.0 g, 66%).

Workup

  1. concentrationconcentrated
  2. stirringto stir for 2 h
  3. concentrationconcentrated
  4. customThe mixture was azeotroped several times with toluene
  5. filtrationThe mixture was filtered
  6. customthe solid was dried

Sources & evidence

ORD record
ord-019e47bea35141638586eb452056b141
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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