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

HRID 1529219Notes

Reaction equation

HRID 1529219 reaction equation
C[O:2][C:3](=[O:28])[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[Cl:27].[Li+].[OH-]>C1COCC1.O>[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:28])=[O:2])=[C:5]([Cl:27])[CH:6]=2)=[CH:25][CH:24]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 582353234-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-chloro-benzoic acid methyl ester

Product 1

HCID 582352874-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-chloro-benzoic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

The title compound is synthesized according to general procedure GP4 starting from 1.1 g (2.8 mmol) 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-chloro-benzoic acid methyl ester (A-39) using 134 mg (5.6 mmoL) LiOH in a mixture of 100 mL THF and 20 mL water. After completion of the reaction, THF is removed under reduced pressure, the aqueous solution is acidified with 1N HCl to pH ˜1 before the pH is adjusted to 6 with saturated aqueous NaHCO3 solution. The precipitated product is collected by filtration, washed with water and methanol. Yield: 760 mg (72%).

Workup

  1. customis removed under reduced pressure
  2. filtrationThe precipitated product is collected by filtration
  3. washwashed with water and methanol

Sources & evidence

ORD record
ord-bd52328426e0482db01e1ee2d537e347
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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