Tetrahydrofuran → HCID 18987439, compound

HRID 2396493Notes

Reaction equation

HRID 2396493 reaction equation
[CH2:1]([N:3]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([C:12](=[N:14][OH:15])[NH2:13])=[CH:4]1)[CH3:2].[H-].[Na+].C(O[CH:24]1[CH2:29][CH2:28][N:27]([CH3:30])[CH2:26][CH2:25]1)(=O)CCC.[CH2:31]1[CH2:35]OC[CH2:32]1>>[N:27]1([CH2:30][CH2:32][CH2:31][C:35]2[O:15][N:14]=[C:12]([C:5]3[C:6]4[C:11](=[CH:10][CH:9]=[CH:8][CH:7]=4)[N:3]([CH2:1][CH3:2])[CH:4]=3)[N:13]=2)[CH2:26][CH2:25][CH2:24][CH2:29][CH2:28]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 24758Sodium hydrideHCID 3415946HCID 3415946, compoundHCID 98154471-Methylpiperidin-4-yl butanoate

Product 1

HCID 18987439HCID 18987439, compound

Conditions

Temperature
60 °C

Procedure

1-Ethylindole-3-ylcarboxamide oxime (200 mg, 0.98 mmol, prepared by the general method of EP-A-328200) was dissolved in anhydrous THF (4 ml) containing 4-A° powdered molecular sieves (300 mg). The mixture was stirred for 30 mins., sodium hydride (80% dispersion in oil) (40 mg, 1.3 mmol) was added and the mixture was heated at 60° C. for 20 min. It was then cooled to RT and a solution of methyl-4-piperidinyl butyrate (364 mg, 1.98 mmol) in THF (2 mol) was added. The resulting mixture was heated at reflux for 1 hr., cooled, filtered and the filtrate concentrated under vacuum. The residue was purified by column chromatography to give the product (210 mg).

Workup

  1. additioncontaining 4-A° powdered molecular sieves (300 mg)
  2. temperatureIt was then cooled to RT
  3. temperatureThe resulting mixture was heated
  4. temperatureat reflux for 1 hr
  5. temperature, cooled
  6. filtrationfiltered
  7. concentrationthe filtrate concentrated under vacuum
  8. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-8d6e0c7f737a4c96bd1262a7db2fae0b
Source dataset
uspto-grants-1996_02
Patent number
US05492919

Reaction notes

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