Trifluoroacetic acid → (S)-N-(2-fluoro-6-(trifluoromethyl)phenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide

HRID 627044Notes

Reaction equation

HRID 627044 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[NH:12][C:13]([C@H:15]1[N:23]([C:24](=[O:43])[C@@H:25]([NH:29][C:30](=[O:42])[C@@H:31]([N:33](C)[C:34](=O)OC(C)(C)C)[CH3:32])[CH:26]([CH3:28])[CH3:27])[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[CH2:16]1)=[O:14].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([C:8]([F:9])([F:10])[F:11])[C:3]=1[NH:12][C:13]([C@H:15]1[N:23]([C:24](=[O:43])[C@@H:25]([NH:29][C:30](=[O:42])[C@@H:31]([NH:33][CH3:34])[CH3:32])[CH:26]([CH3:27])[CH3:28])[C:18]2=[N:19][CH:20]=[CH:21][CH:22]=[C:17]2[CH2:16]1)=[O:14]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 131735264tert-butyl (S)-1-((S)-1-((S)-2-(2-fluoro-6-(trifluoromethyl)phenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Product 1

HCID 73603779(S)-N-(2-fluoro-6-(trifluoromethyl)phenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamideYield 59.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 50 mL round-bottomed flask, tert-butyl (S)-1-((S)-1-((S)-2-(2-fluoro-6-(trifluoromethyl)phenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (20 mg, 32.8 μmol Eq: 1.00) was combined with DCM (1.5 mL) to give a colorless solution. TFA (500 μL, 6.49 mmol, Eq: 198) was added and the reaction mixture was stirred at rt for 30 min. The crude reaction mixture was concentrated in vacuo. The residue was taken up in DCM, washed with saturated aqueous NaHCO3, dried over Na2SO4 and concentrated in vacuo to give (S)—N-(2-fluoro-6-(trifluoromethyl)phenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide as a white solid (10 mg), m/z=510.

Workup

  1. customto give a colorless solution
  2. customThe crude reaction mixture
  3. concentrationwas concentrated in vacuo
  4. washwashed with saturated aqueous NaHCO3
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-50905993abaa466e8167a55bd2ad8ee0
Source dataset
uspto-grants-2016_04
Patent number
US09309248B2

Reaction notes

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