Sodium Hydroxide → 2-(4-Methyl-2-(piperidin-1-yl)-6-(quinolin-8-yl)pyrimidin-5-yl)pentanoic acid

HRID 1399710Notes

Reaction equation

HRID 1399710 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([O:11]C)=[O:10])=[C:6]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)[N:5]=[C:4]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[N:3]=1.[OH-].[Na+]>CO>[CH3:1][C:2]1[C:7]([CH:8]([CH2:13][CH2:14][CH3:15])[C:9]([OH:11])=[O:10])=[C:6]([C:16]2[CH:17]=[CH:18][CH:19]=[C:20]3[C:25]=2[N:24]=[CH:23][CH:22]=[CH:21]3)[N:5]=[C:4]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[N:3]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 66955319Methyl 2-(4-methyl-2-(piperidin-1-yl)-6-(quinolin-8-yl)pyrimidin-5-yl)pentanoate

Product 1

HCID 509957322-(4-Methyl-2-(piperidin-1-yl)-6-(quinolin-8-yl)pyrimidin-5-yl)pentanoic acidYield 10.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

This compound was prepared according to general method D from methyl 2-(4-methyl-2-(piperidin-1-yl)-6-(quinolin-8-yl)pyrimidin-5-yl)pentanoate (0.057 g; 0.136 mmol), sodium hydroxide 10N solution (0.200 mL; 2.00 mmol) in methanol (2 mL) at 60° C. for 18 h. Purification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane, followed by a purification by preperative HPLC (HPLC method 1) furnished 0.0059 g (9%) of the title compound.

Workup

  1. customThis compound was prepared
  2. customPurification by flash-chromatography on silica gel using a gradient of methanol (1-10%) in dichloromethane
  3. customfollowed by a purification by preperative HPLC (HPLC method 1)

Sources & evidence

ORD record
ord-52a86ade34154fc5b4abd907eff1a4f0
Source dataset
uspto-grants-2014_12
Patent number
US08906906B2

Reaction notes

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