Trifluoroacetic acid → HCID 57479079, compound

HRID 556482Notes

Reaction equation

HRID 556482 reaction equation
C(OC(=O)[NH:7][CH2:8][CH2:9][N:10]([C:14]1([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:24])[CH:11]([CH3:13])[CH3:12])(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[NH2:7][CH2:8][CH2:9][N:10]([CH:11]([CH3:13])[CH3:12])[C:14]1([CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([Cl:32])[CH:27]=2)[C:22]2[C:17](=[CH:18][C:19]([Cl:23])=[CH:20][CH:21]=2)[NH:16][C:15]1=[O:24]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57507319HCID 57507319, compound

Product 1

HCID 57479079HCID 57479079, compoundYield 76.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the solution of rac-(2-{[6-Chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-yl]-isopropyl-amino}-ethyl)-carbamic acid tert-butyl ester (100 mg, 0.2 mmol) in DCM (10 mL) was added TFA (0.3 mL). The mixture was stirred at room temperature for 2 hr, then washed with NaOH solution (5%) and water. The organic layer was dried over Na2SO4, concentrated in vacuo to give 60 mg rac-3-[(2-Amino-ethyl)-isopropyl-amino]-6-chloro-3-(3-chloro-benzyl)-1,3-dihydro-indol-2-one. MS: [M+H]+=392

Workup

  1. washwashed with NaOH solution (5%) and water
  2. dry with materialThe organic layer was dried over Na2SO4
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6819bb7edab0416cbc4fe101d53f7b97
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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