Water → {4-[5-({2-[(5-Cyanopyridin-2-yl)amino]ethyl}amino)-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]piperidin-1-yl}acetic acid

HRID 2088710Notes

Reaction equation

HRID 2088710 reaction equation
C([O:3][C:4](=[O:41])[CH2:5][N:6]1[CH2:11][CH2:10][CH:9]([C:12]2[N:20]=[C:19]3[N:14]([C:15]([NH:29][CH2:30][CH2:31][NH:32][C:33]4[CH:38]=[CH:37][C:36]([C:39]#[N:40])=[CH:35][N:34]=4)=[N:16][C:17]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=4[Cl:28])=[CH:18]3)[N:13]=2)[CH2:8][CH2:7]1)C.O.[OH-].[Na+]>COCCOC>[C:39]([C:36]1[CH:37]=[CH:38][C:33]([NH:32][CH2:31][CH2:30][NH:29][C:15]2[N:14]3[N:13]=[C:12]([CH:9]4[CH2:10][CH2:11][N:6]([CH2:5][C:4]([OH:41])=[O:3])[CH2:7][CH2:8]4)[N:20]=[C:19]3[CH:18]=[C:17]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[N:16]=2)=[N:34][CH:35]=1)#[N:40]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 70252366Ethyl {4-[5-({2-[(5-cyanopyridin-2-yl)amino]ethyl}amino)-7-(2,4-dichlorophenyl)[1,2,4]-triazolo[1,5-c]pyrimidin-2-yl]piperidin-1-yl}acetate

Product 1

HCID 67229276{4-[5-({2-[(5-Cyanopyridin-2-yl)amino]ethyl}amino)-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]piperidin-1-yl}acetic acid

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

105 mg (0.18 mmol) of ethyl-{4-[5-({2-[(5-cyanopyridin-2-yl)amino]ethyl}amino)-7-(2,4-dichlorophenyl)[1,2,4]triazolo[1,5-c]pyrimidin-2-yl]piperidin-1-yl}acetate (Example 57A) were dissolved in 1,2-dimethoxyethane (7.5 ml), water (5 ml) and 31 mg (0.76 mmol) of sodium hydroxide were added and the reaction mixture was stirred at RT for 16 h. The mixture was then concentrated by lyophilization. This gave, after purification of the residue by preparative HPLC (Method 11), 65 mg (65% of theory) of the product as a solid.

Workup

  1. concentrationThe mixture was then concentrated by lyophilization
  2. customThis gave, after purification of the residue by preparative HPLC (Method 11), 65 mg (65% of theory) of the product as a solid

Sources & evidence

ORD record
ord-651a0be84ccf4f8290c3f274d6e39140
Source dataset
uspto-grants-2013_05
Patent number
US08436003B2

Reaction notes

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