Water → HCID 9797606, compound

HRID 1603862Notes

Reaction equation

HRID 1603862 reaction equation
[NH2:1][C:2]1[C:3]([CH3:18])=[C:4]2[C:8](=[CH:9][C:10]=1[CH3:11])[N:7]([CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:6][CH2:5]2.C(N(CC)CC)C.[C:26](Cl)(=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28].O>C(Cl)(Cl)Cl>[CH2:12]([N:7]1[C:8]2[C:4](=[C:3]([CH3:18])[C:2]([NH:1][C:26](=[O:31])[C:27]([CH3:30])([CH3:29])[CH3:28])=[C:10]([CH3:11])[CH:9]=2)[CH2:5][CH2:6]1)[CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 15512444HCID 15512444, compound

Product 1

HCID 9797606HCID 9797606, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

5-Amino-4,6-dimethyl-1-hexylindoline (880 mg) was dissolved in chloroform (20 ml), and triethylamine (370 mg) and pivaloyl chloride (430 mg) were added, which was followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture, and the mixture was washed with saturated brine and dried over sodium sulfate. The solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (developing solvent:chloroform-methanol=1:0-50:1) and recrystallized from ethanol to give 650 mg of the title compound.

Workup

  1. washthe mixture was washed with saturated brine
  2. dry with materialdried over sodium sulfate
  3. customThe solvent was evaporated under reduced pressure
  4. customThe residue was purified by silica gel column chromatography (developing solvent:chloroform-methanol=1:0-50:1)
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-607ffb7107124615b00436d018b8a4a5
Source dataset
uspto-grants-1999_11
Patent number
US05990150

Reaction notes

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