Potassium Carbonate → HCID 178424873, compound

HRID 1532381Notes

Reaction equation

HRID 1532381 reaction equation
[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19]#[N:20])[CH:17]=2)[NH:12][C:11]=1[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=1)([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[NH2:37][OH:38]>C(O)C>[C:1]([O:5][C:6](=[O:29])[NH:7][CH2:8][CH2:9][C:10]1[C:18]2[C:13](=[CH:14][CH:15]=[C:16]([C:19](=[NH:20])[NH:37][OH:38])[CH:17]=2)[NH:12][C:11]=1[C:21]1[CH:26]=[C:25]([CH3:27])[CH:24]=[C:23]([CH3:28])[CH:22]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 443297Hydroxyamine hydrochlorideHCID 69951663{2-[5-cyano-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester

Product 1

HCID 178424873HCID 178424873, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of {2-[5-cyano-2-(3,5-dimethylphenyl)-1H-indol-3-yl]ethyl}carbamic acid tert-butyl ester (300 mg in 5 mL ethanol) was added to a suspension of 725 mg potassium carbonate and 273 mg hydroxylamine hydrochloride in 7 mL ethanol and the whole heated to reflux on an oil bath. After 21 hours, the mixture was cooled to room temperature and filtered to remove solids. The filtrate was concentrated in vacuo then partitioned between ethyl acetate and water. The organic portion was washed with water, dried over sodium sulfate and the concentrate purified by flash chromatography on silica gel (methylene chloride:methanol, 92:8) to give the title compound (105 mg).

Workup

  1. temperaturethe whole heated
  2. temperatureto reflux on an oil bath
  3. filtrationfiltered
  4. customto remove solids
  5. concentrationThe filtrate was concentrated in vacuo
  6. customthen partitioned between ethyl acetate and water
  7. washThe organic portion was washed with water
  8. dry with materialdried over sodium sulfate
  9. customthe concentrate purified by flash chromatography on silica gel (methylene chloride:methanol, 92:8)

Sources & evidence

ORD record
ord-4cdce0e500b341eca329812c45fc85c9
Source dataset
uspto-grants-2001_03
Patent number
US06200957B1

Reaction notes

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