Trifluoroacetic acid → HCID 57691248, Verbindung

HRID 1513748Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1513748
[Cl:1][C:2]1[CH:7]=[C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH2:17][NH:18][C:19]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][N:27]=5)[N:22]=[CH:21][CH:20]=4)=[N:15][N:16]=3)[N:13]=2)[CH:5]=[CH:4][C:3]=1[CH2:31][NH:32]C(=O)OC(C)(C)C.C(O)(C(F)(F)F)=O>C(Cl)Cl.C(#N)C.O.[OH-].[Na+]>[NH2:32][CH2:31][C:3]1[CH:4]=[CH:5][C:6]([C:8]2[CH:9]=[CH:10][C:11]3[N:12]([C:14]([CH2:17][NH:18][C:19]4[C:28]5[C:23](=[CH:24][C:25]([O:29][CH3:30])=[CH:26][N:27]=5)[N:22]=[CH:21][CH:20]=4)=[N:15][N:16]=3)[N:13]=2)=[CH:7][C:2]=1[Cl:1]

Komponenten

6

Edukt 2

HCID 6422Trifluoroacetic acidHCID 67967034Tert-butyl (2-chloro-4-(3-((7-methoxy-1,5-naphthyridin-4-ylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methylcarbamate

Produkt 1

HCID 57691248HCID 57691248, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 14798Sodium HydroxideKatalysatorHCID 6344DichloromethaneLösungsmittelHCID 18373917Acetonitrile--water (1/1)Lösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a stirring solution of tert-butyl (2-chloro-4-(3-((7-methoxy-1,5-naphthyridin-4-ylamino)methyl)-[1,2,4]triazolo[4,3-b]pyridazin-6-yl)phenyl)methylcarbamate (70 mg, 128 μmol) in DCM (2 mL) was added TFA (2 mL). Reaction solution stirred for 30 min at 23° C. Solvents then removed under reduced pressure and residue purified on prep-HPLC using a water/ACN (0.1% TFA) gradient. Resulting solid was dissolved in 1:1 ACN/water (1 mL) and pH adjusted to 10 with 1M NaOH (approx 10 drops). Resulting solid collected by filtration and washed with water (5 mL). MS (ESI pos. ion) m/z: 447 (MH+). Calc'd exact mass for C22H19ClN8O: 446.

Aufarbeitung

  1. customReaction solution
  2. customSolvents then removed under reduced pressure and residue
  3. custompurified
  4. customResulting solid
  5. customResulting solid
  6. filtrationcollected by filtration
  7. washwashed with water (5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-59e4a52ba1df47a194686de1db0adc88
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08217177B2

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