Lithium Hydroxide → 2-(4-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yloxy)phenyl)acetic acid

HRID 2047033Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2047033
[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:6]2[N:5]=[C:4]([O:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]([O:31]C)=[O:30])=[CH:24][CH:23]=2)[C:3]=1[Br:33].[Li+].[OH-]>C1COCC1>[NH2:1][C:2]1[N:7]2[N:8]=[CH:9][C:10]([C:11]3[CH:12]=[N:13][C:14]4[C:19]([CH:20]=3)=[CH:18][CH:17]=[CH:16][CH:15]=4)=[C:6]2[N:5]=[C:4]([O:21][C:22]2[CH:23]=[CH:24][C:25]([CH2:28][C:29]([OH:31])=[O:30])=[CH:26][CH:27]=2)[C:3]=1[Br:33]

Komponenten

4

Edukt 2

HCID 3939Lithium HydroxideHCID 67494274Methyl 2-(4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yloxy)phenyl)acetate

Produkt 1

HCID 667333442-(4-(7-Amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yloxy)phenyl)acetic acid

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Crude compound, methyl 2-(4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yloxy)phenyl)acetate from step E was dissolved in THF (5 mL) and LiOH (1N, 1 mL) was added. The mixture was stirred at room temperature overnight. The solvent was removed under vacuo, and the resulting residue was taken over with water and the pH value was adjusted to 5˜6. The solid was collected with filtration and purified with HPLC gave the product, 2-(4-(7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yloxy)phenyl)acetic acid. HPLC-MS tR=1.53 min (UV254 nm); Mass calculated for formula C23H16BrN5O3, 489.0, observed LCMS m/z 490.0 (M+H).

Aufarbeitung

  1. customThe solvent was removed under vacuo
  2. filtrationThe solid was collected with filtration
  3. custompurified with HPLC

Quellen und Nachweise

ORD-Eintrag
ord-b30a44cd17f047a2814fe45a0196e72b
Quelldatensatz
uspto-grants-2013_11
Patentnummer
US08591943B2

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