Ethyl Acetate → HCID 22319558, compound

HRID 497621Notes

Reaction equation

HRID 497621 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:19][O:20][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.C(OCC)(=O)C>O1CCCC1>[CH3:19][O:20][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

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 22319621HCID 22319621, compound

Product 1

HCID 22319558HCID 22319558, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
66 °C

Procedure

13.6 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 1 g of N-[6-(4-methoxyphenyl)-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-indazol-3-yl]butanamide, described previously, in 30 cm3 of tetrahydrofuran, and the reaction medium is then heated at about 66° C. for 19 hours. The heating is then stopped and 75 cm3 of ethyl acetate are added. This mixture is washed with 2×50 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 50 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered and concentrated to dryness under reduced pressure (2 kPa; 50° 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 an ethyl acetate/cyclohexane 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 and washed with 2×5 cm3 of diisopropyl ether and then with 2×5 cm3 of ethyl acetate; after drying (90 Pa; 50° C.), 500 mg of N-[6-(4-methoxyphenyl)-1H-indazol-3-yl]butanamide are obtained in the form of a white product melting at 210° C.

Workup

  1. washThis mixture is washed with 2×50 cm3 of saturated aqueous sodium hydrogen carbonate solution
  2. dry with materialThe organic phase is dried over magnesium sulphate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  5. customThe residue is purified by chromatography under an argon pressure of 50 kPa
  6. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with an ethyl acetate/cyclohexane mixture (60/40 by volume)
  7. additionThe fractions containing the expected product
  8. customevaporated under reduced pressure (2 kPa; 50° C.)
  9. filtrationfiltered
  10. washwashed with 2×5 cm3 of diisopropyl ether
  11. dry with materialafter drying (90 Pa; 50° C.), 500 mg of N-[6-(4-methoxyphenyl)-1H-indazol-3-yl]butanamide

Sources & evidence

ORD record
ord-bc3b686e98e84583bc430a1ae1eb4b75
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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