Trifluoroacetic acid → HCID 68538074, compound

HRID 2389356Notes

Reaction equation

HRID 2389356 reaction equation
[C:1]1([CH:7]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:35])[N:12]([CH2:14][CH2:15][NH:16][C:17]([C:19]3[CH:27]=[CH:26][CH:25]=[C:24]4[C:20]=3[CH2:21][CH2:22][N:23]4C(OC(C)(C)C)=O)=[O:18])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(O)(C(F)(F)F)=O>>[C:1]1([CH:7]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:35])[N:12]([CH2:14][CH2:15][NH:16][C:17]([C:19]3[C:20]4[CH2:21][CH2:22][NH:23][C:24]=4[CH:25]=[CH:26][CH:27]=3)=[O:18])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

3

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68538190HCID 68538190, compound

Product 1

HCID 68538074HCID 68538074, compoundYield 82.7%

Procedure

The mixture of tert-butyl 4-[({2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}amino)carbonyl]-1-indolinecarboxylate (142 mg) and TFA (4.0 mL) was stood at ambient temperature for 10 minutes. The resulting mixture was evaporated in vacuo and saturated NaHCO3 aqueous solution (5.0 mL) was added to the residue. The aqueous solution was extracted with EtOAc (10 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford N-{2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}-4-indolinecarboxamide (96 mg) as an yellow amorphous.

Workup

  1. customThe resulting mixture was evaporated in vacuo and saturated NaHCO3 aqueous solution (5.0 mL)
  2. additionwas added to the residue
  3. extractionThe aqueous solution was extracted with EtOAc (10 mL)
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-5bacf0d2daaa4bdca0a5bd7e3526f757
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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