Hydrogen chloride-ethyl acetate → HCID 57663909, compound

HRID 1510248Notes

Reaction equation

HRID 1510248 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:12]=[CH:11][C:10]([NH:13][C:14]([CH:16]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]3C(OC(C)(C)C)=O)=[O:15])=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C(OCC)(=O)C.Cl>C(OCC)(=O)C.CCCCCC>[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[CH:8]=[CH:9][C:10]([NH:13][C:14]([CH:16]3[CH2:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[NH:17]3)=[O:15])=[CH:11][CH:12]=2)=[CH:3][CH:2]=1

Participants

5

Reactant 2

HCID 21866389Hydrogen chloride-ethyl acetateHCID 69075503HCID 69075503, compound

Product 1

HCID 57663909HCID 57663909, compoundYield 105.4%

Reagents, catalysts & solvents 2

HCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of N-[4-(4-pyridinyl)phenyl]-1-tert-butoxycarbonylindoline-2-carboxamide (100 mg) in ethyl acetate (0.60 mL) was added 4N hydrogen chloride-ethyl acetate (2.41 mL) and the mixture was stirred at ambient temperature for 1.5 hours. The resulting mixture was diluted with n-hexane (6.0 mL) and the solid was collected by filtration, and then washed with ethyl acetate/n-hexane (1:2, 1.0 mL) to give N-[4-(4-pyridinyl)phenyl]indoline-2-carboxamide (80 mg) as off-white crystals.

Workup

  1. filtrationthe solid was collected by filtration
  2. washwashed with ethyl acetate/n-hexane (1:2, 1.0 mL)

Sources & evidence

ORD record
ord-b789b821f8624cc592157961835bea51
Source dataset
uspto-grants-2012_07
Patent number
US08211919B2

Reaction notes

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