Trifluoroacetic acid → 1-Acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carboxamide

HRID 273865Notes

Reaction equation

HRID 273865 reaction equation
FC(F)(F)C(O)=O.[C:8]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([CH2:23][CH:24]([N:26]([CH2:34][CH2:35][O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH2:44][CH3:45])C(OC(C)(C)C)=O)[CH3:25])=[CH:17][C:18]=2[C:20]([NH2:22])=[O:21])[CH2:13][CH2:12]1)(=[O:10])[CH3:9].C(=O)(O)[O-].[Na+]>C(Cl)Cl>[C:8]([N:11]1[C:19]2[C:14](=[CH:15][C:16]([CH2:23][CH:24]([NH:26][CH2:34][CH2:35][O:36][C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][C:38]=3[O:43][CH2:44][CH3:45])[CH3:25])=[CH:17][C:18]=2[C:20]([NH2:22])=[O:21])[CH2:13][CH2:12]1)(=[O:10])[CH3:9]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 152252041-acetyl-5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carboxamide

Product 1

HCID 152252051-Acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carboxamideYield 101.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a mixture of trifluoroacetic acid (0.2 ml) and methylene chloride (0.2! ml) was added a solution of 1-acetyl-5-[2-[N-tert-butoxycarbonyl-2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carboxamide (40 mg) in methylene chloride (0.2 ml) with stirring under ice cooling, and the mixture was stirred at room temperature for 1.5 hours. To the reaction mixture was added a saturated aqueous sodium bicarbonate solution, and the mixture was extracted with methylene chloride. The extract was dried over anhydrous magnesium sulfate. The solvent was concentrated under reduced pressure, and the residue was purified by medium pressure liquid column chromatography on silica gel using a mixture of methylene chloride and methanol (10/1) as eluent to give 33 mg of 1-acetyl-5-[2-[2-(2-ethoxyphenoxy)ethylamino]propyl]indoline-7-carboxamide as an amorphous powder.

Workup

  1. stirringthe mixture was stirred at room temperature for 1.5 hours
  2. extractionthe mixture was extracted with methylene chloride
  3. dry with materialThe extract was dried over anhydrous magnesium sulfate
  4. concentrationThe solvent was concentrated under reduced pressure
  5. customthe residue was purified by medium pressure liquid column chromatography on silica gel using
  6. additiona mixture of methylene chloride and methanol (10/1) as eluent

Sources & evidence

ORD record
ord-7405ef4dd820487a9f25f840869c860d
Source dataset
uspto-grants-1995_02
Patent number
US05387603

Reaction notes

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