tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-7-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate → (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-7-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine

HRID 338934Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 338934
[F:1][C:2]([F:42])([F:41])[C@H:3]([N:28]1[CH2:32][CH2:31][C@H:30]([NH:33]C(=O)OC(C)(C)C)[CH2:29]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:24][CH:25]([CH3:27])[CH3:26])=[C:18]([F:23])[CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1>C(O)(C(F)(F)F)=O>[F:42][C:2]([F:1])([F:41])[C@H:3]([N:28]1[CH2:32][CH2:31][C@H:30]([NH2:33])[CH2:29]1)[C:4]1[CH:5]=[CH:6][C:7]2[N:8]([C:10]([C:13]3[CH:22]=[CH:21][C:20]4[C:15](=[CH:16][C:17]([O:24][CH:25]([CH3:27])[CH3:26])=[C:18]([F:23])[CH:19]=4)[N:14]=3)=[N:11][N:12]=2)[CH:9]=1

Komponenten

3

Edukt 1

HCID 86707459tert-butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-7-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate

Produkt 1

HCID 70984789(S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-7-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amineAusbeute 64,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6422Trifluoroacetic acidLösungsmittel

Versuchsvorschrift

tert-Butyl (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-7-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-ylcarbamate (280 mg, 0.476 mmol) was stirred in TFA (3 mL) for 1 hour then concentrated. The residue was dissolved in minimum methanol and added dropwise to a 4N HCl in ether solution. The resulting solid was filtered and dried to yield (S)-1-((R)-2,2,2-trifluoro-1-(3-(6-fluoro-7-isopropoxyquinolin-2-yl)-[1,2,4]triazolo[4,3-a]pyridin-6-yl)ethyl)pyrrolidin-3-amine (150 mg, 64.6% yield) hydrochloride as an off-white solid. LCMS APCI (+) m/z 489 (M+H).

Aufarbeitung

  1. concentrationthen concentrated
  2. dissolutionThe residue was dissolved in minimum methanol
  3. additionadded dropwise to a 4N HCl in ether solution
  4. filtrationThe resulting solid was filtered
  5. customdried

Quellen und Nachweise

ORD-Eintrag
ord-8a5f8a7d4be2402682ba1e442f7f62d8
Quelldatensatz
uspto-grants-2014_11
Patentnummer
US08889704B2

Notizen zur Reaktion

Wird geladen…