Ethyl Acetate → HCID 10040883, compound

HRID 497640Notes

Reaction equation

HRID 497640 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH2:19]([C:21]1[CH:26]=[CH:25][C:24]([C:27]2[CH:35]=[C:34]3[C:30]([C:31]([NH:44][C:45](=[O:49])[CH2:46][CH2:47][CH3:48])=[N:32][N:33]3COCC[Si](C)(C)C)=[CH:29][CH:28]=2)=[CH:23][CH:22]=1)[CH3:20].C(OCC)(=O)C>O1CCCC1>[CH2:19]([C:21]1[CH:22]=[CH:23][C:24]([C:27]2[CH:35]=[C:34]3[C:30]([C:31]([NH:44][C:45](=[O:49])[CH2:46][CH2:47][CH3:48])=[N:32][NH:33]3)=[CH:29][CH:28]=2)=[CH:25][CH:26]=1)[CH3:20]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 22319583HCID 22319583, compound

Product 1

HCID 10040883HCID 10040883, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
67 °C

Procedure

3.3 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to a solution of 240 mg of N-[6-(4-ethylphenyl)-1-[[2-(trimethylsilyl)ethoxy]-methyl]-1H-indazol-3-yl]butanamide, described previously, in 20 cm3 of tetrahydrofuran. The medium is then maintained at 67° C. for 17 hours, and the resulting mixture is then allowed to return to room temperature and 50 cm3 of ethyl acetate are added. The organic phase is washed with 2×50 cm3 of saturated aqueous sodium hydrogen carbonate solution and with 2×50 cm3 of water, separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 45° C.). The residue is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (60/40 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.). The residue is taken up in 10 cm3 of diisopropyl ether, filtered off on a sinter funnel and washed successively with 2 cm3 of ethyl acetate and then with 10 cm3 of diisopropyl ether. After drying (90 Pa; 50° C.), 80 mg of N-[6-(4-ethylphenyl)-1H-indazol-3-yl]butanamide are obtained in the form of a white solid melting at 210° C.

Workup

  1. customto return to room temperature
  2. washThe organic phase is washed with 2×50 cm3 of saturated aqueous sodium hydrogen carbonate solution and with 2×50 cm3 of water
  3. customseparated out
  4. dry with materialdried over magnesium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness under reduced pressure (2 kPa; 45° C.)
  7. customThe residue is purified by chromatography under an argon pressure of 50 kPa
  8. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (60/40 by volume)
  9. additionThe fractions containing the expected product
  10. customevaporated under reduced pressure (2 kPa; 50° C.)
  11. filtrationfiltered off on a sinter funnel
  12. washwashed successively with 2 cm3 of ethyl acetate
  13. dry with materialAfter drying (90 Pa; 50° C.), 80 mg of N-[6-(4-ethylphenyl)-1H-indazol-3-yl]butanamide

Sources & evidence

ORD record
ord-f0cde576dea24aaa956804073020dbfa
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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