HCID 59145276, compound → HCID 59145242, compound

HRID 2389379Notes

Reaction equation

HRID 2389379 reaction equation
[C:1]1([CH:7]([C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:36])[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]4[CH2:28][C:29]([O:31]C(C)(C)C)=[O:30])=[O:18])[CH:13]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>C(O)(C(F)(F)F)=O>[C:37]1([CH:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:9]=[CH:10][C:11](=[O:36])[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]4[CH2:28][C:29]([OH:31])=[O:30])=[O:18])[CH:13]=2)[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1

Participants

3

Reactant 1

HCID 59145276HCID 59145276, compound

Product 1

HCID 59145242HCID 59145242, compoundYield 66.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The mixture of tert-butyl {4-[({2-[5-(diphenylmethyl)-2-oxo-1(2H)-pyridinyl]ethyl}amino)carbonyl]-2,3-dihydro-1H-indol-1-yl}acetate (75 mg) in TFA (2.1 mL) was stood at ambient temperature for 1 hour. The resulting mixture was evaporated in vacuo and was added saturated NaHCO3 aqueous solution (5.0 mL). The aqueous solution was extracted with chloroform (10 mL). The organic layer was washed with brine, dried over anhydrous MgSO4, filtered and evaporated in vacuo to afford {4-[({2-[5-(diphenylmethyl)-2-oxo-1(2H) -pyridinyl]ethyl}amino)carbonyl]-2,3-dihydro-1H-indol-1-yl}acetic acid (45 mg) as an yellow amorphous.

Workup

  1. customThe resulting mixture was evaporated in vacuo
  2. additionwas added saturated NaHCO3 aqueous solution (5.0 mL)
  3. extractionThe aqueous solution was extracted with chloroform (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-8745d179f2ac4a00aca6dacf399c54b2
Source dataset
uspto-grants-2012_09
Patent number
US08273745B2

Reaction notes

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