Triethylamine → HCID 5273214, compound

HRID 1792751Notes

Reaction equation

HRID 1792751 reaction equation
[CH:1](=[N:8][OH:9])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.ClN1C(=O)CCC1=O.[CH2:18]([O:20][N:21]=[CH:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([O:30][CH2:31][CH2:32][CH2:33][C:34]#[CH:35])=[C:25]([CH3:36])[CH:24]=1)[CH3:19].C(N(CC)CC)C>CN(C=O)C.N1C=CC=CC=1>[CH2:18]([O:20][N:21]=[CH:22][C:23]1[CH:28]=[C:27]([CH3:29])[C:26]([O:30][CH2:31][CH2:32][CH2:33][C:34]2[O:9][N:8]=[C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH:35]=2)=[C:25]([CH3:36])[CH:24]=1)[CH3:19]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 12143(Z)-Benzaldehyde oximeHCID 31398ChlorosuccinimideHCID 86760175HCID 86760175, compound

Product 1

HCID 5273214HCID 5273214, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineCatalystHCID 6228DimethylformamideSolvent4×

Procedure

A solution of benzaldehyde oxime (45 mg, 0.372 mmol) in DMF (0.5 ml) was added dropwise to a solution of N-chlorosuccinimide (50 mg, 0.374 mmol) and pyridine (1 drop) in DMF (0.5 ml), keeping the temperature between 25-30° C. The resulting solution was allowed to stir at room temperature for 90 minutes. To this was added a solution of 3,5-dimethyl-4-(4-pentyn-1-yloxy)benzaldehyde O-ethyl oxime (49 mg, 0.189 mmol) in DMF (0.5 mL, the resulting solution was then heated at 85-90° C. for 10 minutes. To this was added, dropwise over 10 minutes, a solution of triethylamine (54 μl, 0.386 mmol) in DMF (0.5 ml), the resulting solution was then heated at 85-90° C. for 1 hour. The reaction was cooled and the solvent removed in vacuo. The residue was partitioned between ethyl acetate (50 ml) and water (15 ml). The organic phase was washed with brine (15 mL), dried (MgSO4), filtered and concentrated in vacuo. Purification by flash chromatography (Ethyl acetate/Hexane 5%) gave the product (Compound 127) as a clear oil (23 mg, 32%). The structure was confirmed by the 1H nmr spectrum which is given in Table 11 below.

Workup

  1. custombetween 25-30° C
  2. temperaturethe resulting solution was then heated at 85-90° C. for 10 minutes
  3. additionTo this was added, dropwise over 10 minutes
  4. temperatureThe reaction was cooled
  5. customthe solvent removed in vacuo
  6. customThe residue was partitioned between ethyl acetate (50 ml) and water (15 ml)
  7. washThe organic phase was washed with brine (15 mL)
  8. dry with materialdried (MgSO4)
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customPurification by flash chromatography (Ethyl acetate/Hexane 5%)

Sources & evidence

ORD record
ord-9a6681b884134483bf8b684de6addf88
Source dataset
uspto-grants-2006_07
Patent number
US07078403B1

Reaction notes

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