Trifluoroacetic acid → (Z)-4-amino-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]cyclohexanecarboxamide

HRID 382037Notes

Reaction equation

HRID 382037 reaction equation
C(OC(=O)[NH:7][CH:8]1[CH2:13][CH2:12][CH:11]([C:14](=[O:38])[NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:30]=[CH:29][CH:28]=[C:27]4[C:23]=3/[C:24](=[CH:32]/[C:33]3[NH:34][CH:35]=[CH:36][CH:37]=3)/[C:25](=[O:31])[NH:26]4)[CH:17]=2)[CH2:10][CH2:9]1)(C)(C)C.FC(F)(F)C(O)=O>C(Cl)Cl.C(OCC)(=O)C>[NH2:7][CH:8]1[CH2:9][CH2:10][CH:11]([C:14]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([C:22]3[CH:30]=[CH:29][CH:28]=[C:27]4[C:23]=3/[C:24](=[CH:32]/[C:33]3[NH:34][CH:35]=[CH:36][CH:37]=3)/[C:25](=[O:31])[NH:26]4)[CH:17]=2)=[O:38])[CH2:12][CH2:13]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 70201180(Z)-[4-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenylcarbamoyl]-cyclohexyl]-carbamic acid tert-butyl ester

Product 1

HCID 59971427(Z)-4-amino-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]cyclohexanecarboxamideYield 40.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the (Z)-[4-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]-phenylcarbamoyl]-cyclohexyl]-carbamic acid tert-butyl ester (51.4 mg, 0.098 mmol) in 3 mL of methylene chloride was then treated with 2 mL of trifluoroacetic acid. The reaction mixture was stirred at room temperature for 1 h, and the reaction mixture was diluted with 50 mL of ethyl acetate. The organic phase was carefully washed with a saturated aqueous sodium bicarbonate solution (3×20 mL), dried over sodium sulfate, filtered, and concentrated in vacuo to provide a yellow-brown solid. This crude solid was washed with 70% chloroform-hexanes, and the insoluble solid was collected by suction filtration to provide pure (Z)-4-amino-N-[3-[2,3-dihydro-2-oxo-3-[(1H-pyrrol-2-yl)methylene]-1H-indol-4-yl]phenyl]cyclohexanecarboxamide (yield: 17 mg, 40%) as a yellow solid (mp 210-212° C.).

Workup

  1. washThe organic phase was carefully washed with a saturated aqueous sodium bicarbonate solution (3×20 mL)
  2. dry with materialdried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. customto provide a yellow-brown solid
  6. washThis crude solid was washed with 70% chloroform-hexanes
  7. filtrationthe insoluble solid was collected by suction filtration

Sources & evidence

ORD record
ord-6f18280a93f54a7abe878d39ff140154
Source dataset
uspto-grants-2001_10
Patent number
US06307056B1

Reaction notes

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