1-Tert-butyl 2-ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)indoline-1,2-dicarboxylate → Ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)indoline-2-carboxylate

HRID 1960445

Reaction equation

HRID 1960445 reaction equation
[CH:1]1([N:4]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)(=[O:33])=[O:32])[C:5]2[CH:6]=[C:7]([O:26][CH2:27][CH2:28][O:29][CH3:30])[CH:8]=[C:9]3[C:13]=2[N:12](C(OC(C)(C)C)=O)[CH:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:10]3)[CH2:3][CH2:2]1>C(OCC)(=O)C.Cl>[CH:1]1([N:4]([S:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][N:35]=2)(=[O:33])=[O:32])[C:5]2[CH:6]=[C:7]([O:26][CH2:27][CH2:28][O:29][CH3:30])[CH:8]=[C:9]3[C:13]=2[NH:12][CH:11]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:10]3)[CH2:2][CH2:3]1

Participants

3

Reactant 1

HCID 591360161-Tert-butyl 2-ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)indoline-1,2-dicarboxylate

Product 1

HCID 59136057Ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)indoline-2-carboxylateYield 96%

Reagents, catalysts & solvents 1

HCID 21866389Hydrogen chloride-ethyl acetateSolvent

Procedure

1-tert-Butyl 2-ethyl 7-[cyclopropyl(pyridin-2-ylsulfonyl)amino]-5-(2-methoxyethoxy)indoline-1,2-dicarboxylate (1.70 g) was added to 4N hydogen chloride-ethyl acetate solution (50 mL), and the mixture was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was diluted with ethyl acetate and aqueous sodium bicarbonate solution. The organic layer was washed with saturated brine, dried over anhydrous sodium sulfate, and filtered, and the filtrate was concentrated under reduced pressure to give the title compound (1.34 g, yield 96%) as a pale-yellow amorphous solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. additionthe residue was diluted with ethyl acetate and aqueous sodium bicarbonate solution
  3. washThe organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-55858cb968b441629aeb84d44fdd1110
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Linked notes

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