Hydrazine hydrate (1:1) → HCID 178474054, compound

HRID 537053Notes

Reaction equation

HRID 537053 reaction equation
[C:1]([C:4]1[N:5]=[C:6]([C:16]2[C:21]([CH3:22])=[CH:20][N:19]=[C:18]([NH:23][C:24](=[O:26])[CH3:25])[CH:17]=2)[O:7][C:8]=1[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[Cl:15])(=O)[CH3:2].C[N:28]([CH:30](OC)OC)C.O.[NH2:36]N>C1(C)C=CC=CC=1>[Cl:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[C:8]1[O:7][C:6]([C:16]2[C:21]([CH3:22])=[CH:20][N:19]=[C:18]([NH:23][C:24](=[O:26])[CH3:25])[CH:17]=2)=[N:5][C:4]=1[C:1]1[CH:2]=[CH:30][NH:28][N:36]=1

Participants

5

Reactant 3

HCID 24654Hydrazine hydrate (1:1)HCID 78373Dimethylformamide dimethyl acetal2×HCID 66749802HCID 66749802, compound

Product 1

HCID 178474054HCID 178474054, compoundYield 359.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

A solution of N-{4-[4-acetyl-5-(2-chlorophenyl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (0.12 g, 0.24 mmol) and DMF-DMA (0.84 mL, 0.63 mmol) in toluene (0.5 mL) was allowed to stir at 100° C. for 5 days, during which time several additional portions of DMF-DMA were added. The reaction mixture was concentrated and the residue was redissolved in AcOH (2 mL). Hydrazine hydrate (0.13 mL, 2.63 mmol) was added and the reaction mixture was allowed to stir at 100° C. for 4 days. The reaction mixture was concentrated and the residue was purified by column chromatography to give N-{4-[5-(2-chlorophenyl)-4-(1H-pyrazol-3-yl)-1,3-oxazol-2-yl]-5-methylpyridin-2-yl}acetamide (Compound I-30) (0.34 g, 35%). LCMS (FA): m/z=394 (M+H).

Workup

  1. additionwere added
  2. concentrationThe reaction mixture was concentrated
  3. dissolutionthe residue was redissolved in AcOH (2 mL)
  4. concentrationThe reaction mixture was concentrated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-cdbf05fc762840ccb6deff8e757601f9
Source dataset
uspto-grants-2014_10
Patent number
US08859768B2

Reaction notes

Loading…