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

HRID 627040Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 627040
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@H:11]1[N:19]([C:20](=[O:39])[C@@H:21]([NH:25][C:26](=[O:38])[C@@H:27]([N:29](C)[C:30](=O)OC(C)(C)C)[CH3:28])[CH:22]([CH3:24])[CH3:23])[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH2:12]1)=[O:10].C(O)(C(F)(F)F)=O>C(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C@H:11]1[N:19]([C:20](=[O:39])[C@@H:21]([NH:25][C:26](=[O:38])[C@@H:27]([NH:29][CH3:30])[CH3:28])[CH:22]([CH3:23])[CH3:24])[C:14]2=[N:15][CH:16]=[CH:17][CH:18]=[C:13]2[CH2:12]1)=[O:10]

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 131735262tert-butyl (S)-1-((S)-1-((S)-2-(2-fluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate

Produkt 1

HCID 73603482(S)-N-(2-fluorophenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamideAusbeute 78,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

In a 50 mL round-bottomed flask, tert-butyl (S)-1-((S)-1-((S)-2-(2-fluorophenylcarbamoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridin-1-yl)-3-methyl-1-oxobutan-2-ylamino)-1-oxopropan-2-yl(methyl)carbamate (39 mg, 72.0 μmol, Eq: 1.00) was combined with DCM (3.00 mL) to give a colorless solution. TFA (1.00 mL, 13.0 mmol, Eq: 180) was added the reaction was stirred at rt for 30 min and then 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-fluorophenyl)-1-((S)-3-methyl-2-((S)-2-(methylamino)propanamido)butanoyl)-2,3-dihydro-1H-pyrrolo[2,3-b]pyridine-2-carboxamide as an off-white solid (25 mg), m/z=442 (M+H).

Aufarbeitung

  1. customto give a colorless solution
  2. concentrationconcentrated in vacuo
  3. washwashed with saturated aqueous NaHCO3
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-480edb7bc125411b864ffb66fafca22b
Quelldatensatz
uspto-grants-2016_04
Patentnummer
US09309248B2

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