Ethyl Acetate → HCID 22319643, compound

HRID 497714Notes

Reaction equation

HRID 497714 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([C:28]3[CH:36]=[C:35]4[C:31]([C:32]([NH:46][C:47](=[O:51])[CH2:48][CH2:49][CH3:50])=[N:33][N:34]4OCOCC[Si](C)(C)C)=[CH:30][CH:29]=3)=[CH:27][C:22]=2CO1.[C:52](OCC)(=[O:54])C>O1CCCC1>[O:19]1[C:23]2[CH:24]=[CH:25][C:26]([C:28]3[CH:36]=[C:35]4[C:31]([C:32]([NH:46][C:47](=[O:51])[CH2:48][CH2:49][CH3:50])=[N:33][NH:34]4)=[CH:30][CH:29]=3)=[CH:27][C:22]=2[O:54][CH2:52]1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 22319695HCID 22319695, compound

Product 1

HCID 22319643HCID 22319643, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
67 °C

Procedure

2 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 600 mg of N-[6-(benzodioxol-5-yl)-1-[[2-(trimethylsilyl)ethoxy]methoxy]-1H-indazol-3-yl]butanamide, described previously, in 12 cm3 of tetrahydrofuran. The medium is then maintained at 67° C. for 16 hours. The mixture is then allowed to return to 19° C. and 60 μm3 of ethyl acetate are added, after which it is washed with 30 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 2×30 cm3 of distilled water and finally with 30 cm3 of saturated aqueous sodium chloride solution. The organic phase is dried over magnesium sulphate, filtered through a sinter funnel and evaporated under reduced pressure (2 kPa; 45° C.). The residue obtained is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 15-40 μm; diameter 3 cm), eluting with a cyclohexane/ethyl acetate mixture (60/40 by volume) and collecting 15 cm3 fractions. The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.). After drying (90 Pa; 50° C.), 260 mg of N-[6-(1,3-benzodioxol-5-yl)-1H-indazol-3-yl]butanamide are obtained in the form of a white solid melting at 240° C.

Workup

  1. customto return to 19° C.
  2. washafter which it is washed with 30 cm3 of saturated aqueous sodium hydrogen carbonate solution
  3. dry with materialThe organic phase is dried over magnesium sulphate
  4. filtrationfiltered through a sinter funnel
  5. customevaporated under reduced pressure (2 kPa; 45° C.)
  6. customThe residue obtained
  7. customis purified by chromatography under an argon pressure of 50 kPa
  8. washon a column of silica gel (particle size 15-40 μm; diameter 3 cm), eluting with a cyclohexane/ethyl acetate mixture (60/40 by volume)
  9. customcollecting 15 cm3 fractions
  10. additionThe fractions containing the expected product
  11. customevaporated under reduced pressure (2 kPa; 50° C.)
  12. dry with materialAfter drying (90 Pa; 50° C.), 260 mg of N-[6-(1,3-benzodioxol-5-yl)-1H-indazol-3-yl]butanamide

Sources & evidence

ORD record
ord-8e7752fe791749e29f0148b7771730da
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

Loading…