Lithium Hydroxide → HCID 67494522, compound

HRID 2047047Notes

Reaction equation

HRID 2047047 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]([CH2:21][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]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([CH2:28][C:29]([OH:31])=[O:30])=[CH:24][CH:23]=2)[C:3]=1[Br:33]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 66735636HCID 66735636, compound

Product 1

HCID 67494522HCID 67494522, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Crude Methyl 2-(4-((7-amino-6-bromo-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidin-5-yl)methyl)phenyl)acetate from step F 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-yl)methyl)phenyl)acetic acid. HPLC-MS tR=1.53 min (UV254 nm); mass calculated for formula C24H18BrN5O2 487.1, observed LCMS m/z 487.9 (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-b2197a36b1624a9b98da22339db04b77
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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