Trifluoroacetic acid → HCID 57955166, Verbindung

HRID 1094911Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1094911
[NH2:1][C:2]1[C:7]2=[C:8]([C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:47])[NH:35][C:36]4[CH:41]=[C:40]([C:42]([F:45])([F:44])[F:43])[CH:39]=[CH:38][C:37]=4[F:46])=[C:29]([F:48])[CH:28]=3)[C:9]([CH2:24][O:25][CH3:26])=[C:10]([CH:11]3[CH2:16][CH2:15][N:14](C(OC(C)(C)C)=O)[CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]1[C:7]2=[C:8]([C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34]([NH:35][C:36]4[CH:41]=[C:40]([C:42]([F:45])([F:43])[F:44])[CH:39]=[CH:38][C:37]=4[F:46])=[O:47])=[C:29]([F:48])[CH:28]=3)[C:9]([CH2:24][O:25][CH3:26])=[C:10]([CH:11]3[CH2:16][CH2:15][NH:14][CH2:13][CH2:12]3)[N:6]2[N:5]=[CH:4][N:3]=1

Komponenten

4

Edukt 2

HCID 6422Trifluoroacetic acidHCID 66641290Tert-butyl 4-{4-amino-5-[3-fluoro-4-({[2-fluoro-5-(trifluoromethyl)phenyl]carbamoyl}amino)phenyl]-6-(methoxymethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl}piperidine-1-carboxylate

Produkt 1

HCID 57955166HCID 57955166, VerbindungAusbeute 70,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a flask charged with tert-butyl 4-{4-amino-5-[3-fluoro-4-({[2-fluoro-5-(trifluoromethyl)phenyl]carbamoyl}amino)phenyl]-6-(methoxymethyl)pyrrolo[2,1-f][1,2,4]triazin-7-yl}piperidine-1-carboxylate was added methylene chloride (12.5 mL). To this suspension was added 12.5 mL of trifluoroacetic acid. The homogeneous solution was allowed to stir at rt under nitrogen for 17 hours. The reaction mixture was concentrated and the residue dissolved in EtOAc. The organic phase was washed with saturated sodium bicarbonate solution (2×), brine (1×), separated and the organic layer dried (Na2SO4). The organic layer was filtered, concentrated and left under vacuum overnight to yield the title compound (150 mg, 70.4% yield). 1H-NMR (DMSO-d6) MS [M+H]+=576; LCMS RT=2.51 min.

Aufarbeitung

  1. concentrationThe reaction mixture was concentrated
  2. dissolutionthe residue dissolved in EtOAc
  3. washThe organic phase was washed with saturated sodium bicarbonate solution (2×), brine (1×)
  4. customseparated
  5. dry with materialthe organic layer dried (Na2SO4)
  6. filtrationThe organic layer was filtered
  7. concentrationconcentrated
  8. waitleft under vacuum overnight

Quellen und Nachweise

ORD-Eintrag
ord-c66161c5b55443568f6211d8a91f6b49
Quelldatensatz
uspto-grants-2012_03
Patentnummer
US08133995B2

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