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

HRID 2047033Notes

Reaction equation

HRID 2047033 reaction equation
[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]

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

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

Sources & evidence

ORD record
ord-b30a44cd17f047a2814fe45a0196e72b
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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