Hydrochloric Acid → 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-methyl-pyridin-4-yl]-benzoic acid

HRID 1529214Notes

Reaction equation

HRID 1529214 reaction equation
C[O:2][C:3](=[O:26])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[CH:15]=[CH:14][N:13]=[C:12]([CH3:16])[C:11]=2[C:17]#[C:18][C:19]2[CH:20]=[N:21][C:22]([NH2:25])=[CH:23][CH:24]=2)=[CH:6][CH:5]=1.[OH-].[Na+].Cl>C1COCC1>[NH2:25][C:22]1[N:21]=[CH:20][C:19]([C:18]#[C:17][C:11]2[C:12]([CH3:16])=[N:13][CH:14]=[CH:15][C:10]=2[C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:26])=[O:2])=[CH:9][CH:8]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 582352434-[3-(6-Amino-pyridin-3-ylethynyl)-2-methyl-pyridin-4-yl]-benzoic acid methyl ester

Product 1

HCID 582353194-[3-(6-Amino-pyridin-3-ylethynyl)-2-methyl-pyridin-4-yl]-benzoic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound is synthesized according to general procedure GP4 starting from 2.0 g (5.8 mmol) 4-[3-(6-amino-pyridin-3-ylethynyl)-2-methyl-pyridin-4-yl]-benzoic acid methyl ester using 11.6 mL (11.6 mmoL) 1 N NaOH in 8 mL THF. After completion of the reaction the pH is adjusted to pH about 5 with 1.0 N HCl. The precipitate is collected by filtration, washed with water and dried under vacuum. The solid is taken up in iPrOH, stirred for a few minutes before the solid is isolated by filtration and dried at 40° C. under vacuum. Yield: 1.9 g (99%).

Workup

  1. customAfter completion of the reaction the pH
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. customis isolated by filtration
  6. customdried at 40° C. under vacuum

Sources & evidence

ORD record
ord-dabc0a9d1e104228a4fbca9ef413c19f
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

Loading…