Hydrazine hydrate (1:1) → HCID 178474061, compound

HRID 537073Notes

Reaction equation

HRID 537073 reaction equation
[C:1]([NH:4][C:5]1[CH:10]=[C:9]([C:11]2[O:12][C:13]([C:17]([NH2:19])=O)=[C:14]([I:16])[N:15]=2)[C:8]([CH3:20])=[CH:7][N:6]=1)(=[O:3])[CH3:2].C[N:22]([CH:24](OC)OC)C.O.[NH2:30]N>C1(C)C=CC=CC=1.O>[I:16][C:14]1[N: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)[O:12][C:13]=1[C:17]1[N:22]=[CH:24][NH:30][N:19]=1

Participants

6

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetalHCID 66749242HCID 66749242, compound

Product 1

HCID 178474061HCID 178474061, compoundYield 98.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

To a slurry of 2-(2-acetamido-5-methylpyridin-4-yl)-4-iodo-1,3-oxazole-5-carboxamide (12.0 g, 31.0 mmol) in toluene (240 mL) was added DMF-DMA (24.0 mL, 187 mmol). The reaction mixture was allowed to stir at 90° C. for 5 h and then concentrated. The residue was suspended in AcOH (120 mL) and hydrazine hydrate (4.8 mL, 155 mmol) was added slowly. The reaction mixture was allowed to stir at rt overnight and then diluted with water. The slurry was filtered and the solid was collected, washed with water, and dried to give N-{4-[4-iodo-5-(1H-1,2,4-triazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (12.5 g, 95%).

Workup

  1. concentrationconcentrated
  2. stirringto stir at rt overnight
  3. filtrationThe slurry was filtered
  4. customthe solid was collected
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-d21f0f73972c403780e2f460d73f9c9d
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

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