Hydrochloric Acid → 3-(6-Aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionic acid

HRID 2370942Notes

Reaction equation

HRID 2370942 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH2:20][C:21]#[C:22][CH3:23])[CH:19]=2)[C:10]([O:12]CC)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+].Cl>C1COCC1>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][CH:9]([C:15]2[N:16]=[CH:17][N:18]([CH2:20][C:21]#[C:22][CH3:23])[CH:19]=2)[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium Hydroxide2×HCID 69331513Ethyl 3-(6-aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionate

Product 1

HCID 114929383-(6-Aminopyridin-3-yl)-2-(1-but-2-ynyl-1H-imidazol-4-yl)propionic acidYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 25 mg (0.08 mmol) of the compound from example 32a in 2 ml of THF was mixed with 88 μl of 1N NaOH and stirred at RT for 4 h. Then, and again after stirring overnight, 40 μl of NaOH were added. After stirring for a further 24 h, the reaction mixture was neutralized with 2N HCl and freeze-dried. Preparative HPLC afforded 5 mg of the title compound as bistrifluoroacetate.

Workup

  1. stirringThen, and again after stirring overnight
  2. stirringAfter stirring for a further 24 h
  3. customfreeze-dried

Sources & evidence

ORD record
ord-cc991dbe73814b228db4d0bf549d0a35
Source dataset
uspto-grants-2014_04
Patent number
US08710232B2

Reaction notes

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