Sodium Hydroxide → HCID 58235232, compound

HRID 1529217Notes

Reaction equation

HRID 1529217 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[F:27].[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:28])=[O:2])=[C:5]([F:27])[CH:6]=2)=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 582352834-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-fluoro-benzoic acid methyl ester

Product 1

HCID 58235232HCID 58235232, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
95 °C

Procedure

The title compound is synthesized according to general procedure GP4 starting from 2.36 g (6.3 mmol) 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-fluoro-benzoic acid methyl ester (A-37) using 9.4 mL (9.4 mmoL) 1N NaOH in 40 mL THF. The reaction mixture is stirred for 2 h at 95° C. The solvent is removed under reduced pressure, the crude product is taken up with water and the pH is adjusted to 5 (with 1N HCl). The precipitate is collected by filtration. Yield after drying: 2.2 g (97%).

Workup

  1. customThe solvent is removed under reduced pressure
  2. filtrationThe precipitate is collected by filtration
  3. customYield
  4. customafter drying

Sources & evidence

ORD record
ord-77b16910e93e43ab941c0c146ecf36b6
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

Loading…