Sodium Hydroxide → 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid

HRID 1529221Notes

Reaction equation

HRID 1529221 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH2:16][CH3:17])[C:11]=2[C:18]#[C:19][C:20]2[CH:21]=[N:22][C:23]([NH2:26])=[CH:24][CH:25]=2)=[CH:6][C:5]=1[O:27][CH3:28].[OH-].[Na+]>C1COCC1>[NH2:26][C:23]1[N:22]=[CH:21][C:20]([C:19]#[C:18][C:11]2[C:12]([CH2:16][CH3:17])=[N:13][CH:14]=[CH:15][C:10]=2[C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[C:5]([O:27][CH3:28])[CH:6]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 582353114-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid methyl ester

Product 1

HCID 582352604-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is synthesized according to general procedure GP4 starting from 1.07 g (2.77 mmol) 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-methoxy-benzoic acid methyl ester (A-41) using 2.4 mL (2.4 mmoL) 1N NaOH in 30 mL THF. The reaction mixture is stirred over night, after complete consumption of the starting material the pH is adjusted to 4 (using 1N HCl). As no precipitate is formed, the aqueous phase is extracted with DCM. However, the product precipitates upon addition of DCM and is collected by filtration. Additional product is precipitated from the mother liquid by adjustment of the pH to 6 (using 1N NaOH). Yield of the combined fractions: 990 mg (96%).

Workup

  1. customafter complete consumption of the starting material the pH
  2. customAs no precipitate is formed
  3. extractionthe aqueous phase is extracted with DCM
  4. customHowever, the product precipitates upon addition of DCM
  5. filtrationis collected by filtration
  6. customAdditional product is precipitated from the mother liquid by adjustment of the pH to 6 (using 1N NaOH)

Sources & evidence

ORD record
ord-774948f6910f496a81659d6a7779630d
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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