Trifluoroacetic acid → HCID 57479100, compound

HRID 556480Notes

Reaction equation

HRID 556480 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][C:15](=[O:43])[C:16]2[CH:21]=[CH:20][C:19]([Br:22])=[CH:18][C:17]=2[NH:23][C:24]2([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=3)[C:32]3[C:27](=[CH:28][C:29]([Cl:33])=[CH:30][CH:31]=3)[NH:26][C:25]2=[O:34])[CH2:10][CH2:9]1)=O)(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[Br:22][C:19]1[CH:20]=[CH:21][C:16]([C:15]([NH:14][CH:11]2[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]2)=[O:43])=[C:17]([NH:23][C:24]2([CH2:35][C:36]3[CH:41]=[CH:40][CH:39]=[C:38]([Cl:42])[CH:37]=3)[C:32]3[C:27](=[CH:28][C:29]([Cl:33])=[CH:30][CH:31]=3)[NH:26][C:25]2=[O:34])[CH:18]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57479097HCID 57479097, compound

Product 1

HCID 57479100HCID 57479100, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of rac-4-{4-Bromo-2-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-benzoylamino}-piperidine-1-carboxylic acid tert-butyl ester (30 mg, 0.044 mmol) in DCM (2 mL) was added TFA (0.5 mL). The mixture was stirred for 3 h, concentrated. The residue was dissolved in DCM, the resulting solution was washed with Na2CO3 solution, dried with Na2SO4, concentrated to give 22 mg rac-4-Bromo-2-[6-chloro-3-(3-chloro-benzyl)-2-oxo-2,3-dihydro-1H-indol-3-ylamino]-N-piperidin-4-yl-benzamide. MS: [M+H]+=587

Workup

  1. concentrationconcentrated
  2. dissolutionThe residue was dissolved in DCM
  3. washthe resulting solution was washed with Na2CO3 solution
  4. dry with materialdried with Na2SO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-69224c8777294ffbb591a3f19120d72a
Source dataset
uspto-grants-2011_11
Patent number
US08058269B2

Reaction notes

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