Water → HCID 135449000, compound

HRID 2268172Notes

Reaction equation

HRID 2268172 reaction equation
C(O)(=O)/C=C\C(O)=O.C1(CN2CCC(C[CH2:23][C:24]3[C:28]4[CH:29]=[C:30]5[CH2:35][C:34](=[O:36])[NH:33][C:31]5=[CH:32][C:27]=4[O:26][N:25]=3)CC2)C=CC=CC=1.N1C=CC=CC=1.O>CN(C)C=O>[CH3:23][C:24]1[C:28]2[CH:29]=[C:30]3[CH2:35][C:34](=[O:36])[NH:33][C:31]3=[CH:32][C:27]=2[O:26][N:25]=1

Participants

5

Reactant 3

HCID 962WaterHCID 1049PyridineHCID 135462830145815-98-1

Product 1

HCID 135449000HCID 135449000, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
127.5 °C

Procedure

A mixture of the oxime acetate formed in step c (4.48 g, 18.0 mmol) and pyridine (14.6 mL, 180 mmol) in dimethylformamide (DMF) (660 mL) was heated at 125-130° C. for 4 hours. The cooled reaction mixture was poured over water and extracted with EtOAc (4 times). The combined organic layer was washed with water and brine and dried (MgSO4), filtered, and concentrated. Purification by silica gel flash chromatography (50% EtOAc/hexanes→100% EtOAc) gave the title compound (2.20 g, 65%) as a pale yellow-orange solid.

Workup

  1. customThe cooled reaction mixture
  2. extractionextracted with EtOAc (4 times)
  3. washThe combined organic layer was washed with water and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification by silica gel flash chromatography (50% EtOAc/hexanes→100% EtOAc)

Sources & evidence

ORD record
ord-8cf4c7f019ff4d90a7f528d620dc0f12
Source dataset
uspto-grants-2001_12
Patent number
US06326382B1

Reaction notes

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