Ethyl Acetate → HCID 22319511, compound

HRID 497687Notes

Reaction equation

HRID 497687 reaction equation
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Cl:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([NH:37][C:38](=[O:42])[CH2:39][CH2:40][CH3:41])=[N:25][N:26]2COCC[Si](C)(C)C)=[CH:22][C:21]=1[C:43]1[CH:48]=[CH:47][C:46]([CH3:49])=[CH:45][CH:44]=1.C(OCC)(=O)C>O1CCCC1>[Cl:19][C:20]1[CH:28]=[C:27]2[C:23]([C:24]([NH:37][C:38](=[O:42])[CH2:39][CH2:40][CH3:41])=[N:25][NH:26]2)=[CH:22][C:21]=1[C:43]1[CH:44]=[CH:45][C:46]([CH3:49])=[CH:47][CH:48]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 2724141Tetrabutylammonium FluorideHCID 22319611HCID 22319611, compound

Product 1

HCID 22319511HCID 22319511, compoundYield 31.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

11.4 cm3 of tetrabutylammonium fluoride as a 1M solution in tetrahydrofuran are added to 870 mg of N-[6-chloro-5-(4-methylphenyl)-1-[[2-(trimethylsilyl)ethoxy]-methyl]-1H-indazol-3-yl]butanamide, described previously, in 20 cm3 of tetrahydrofuran. The medium is then refluxed for 20 hours and the mixture is then allowed to return to room temperature and 20 cm3 of ethyl acetate are added; the organic phase is washed with 2×20 cm3 of saturated aqueous sodium hydrogen carbonate solution and then with 2×20 cm3 of saturated aqueous sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and evaporated to dryness under reduced pressure (2 kPa; 45° C.). The residue is taken up in 10 cm3 of diethyl ether, filtered off on a sinter funnel and then dried under reduced pressure (90 Pa; 50° C.) to give 195 mg of N-[6-chloro-5-(4-methylphenyl)-1H-indazol-3-yl]butanamide in the form of a beige-coloured powder.

Workup

  1. temperatureThe medium is then refluxed for 20 hours
  2. customto return to room temperature
  3. washthe organic phase is washed with 2×20 cm3 of saturated aqueous sodium hydrogen carbonate solution
  4. customThe organic phase is separated out
  5. dry with materialdried over magnesium sulphate
  6. filtrationfiltered
  7. customevaporated to dryness under reduced pressure (2 kPa; 45° C.)
  8. filtrationfiltered off on a sinter funnel
  9. customdried under reduced pressure (90 Pa; 50° C.)

Sources & evidence

ORD record
ord-4d186d49926444d3922533caaaa9a2d3
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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