Tetrahydrofuran → 4-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-benzoic acid

HRID 1529224Notes

Reaction equation

HRID 1529224 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+].[CH2:31]1COCC1>>[CH2:16]([C:12]1[C:11]([C:18]#[C:19][C:20]2[CH:21]=[N:22][C:23]([NH:26][CH3:31])=[CH:24][CH:25]=2)=[C:10]([C:7]2[CH:8]=[CH:9][C:4]([C:3]([OH:2])=[O:28])=[C:5]([F:27])[CH:6]=2)[CH:15]=[CH:14][N:13]=1)[CH3:17]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 582352834-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-fluoro-benzoic acid methyl ester

Product 1

HCID 667708384-[2-Ethyl-3-(6-methylamino-pyridin-3-ylethynyl)-pyridin-4-yl]-2-fluoro-benzoic acid

Conditions

Temperature
65 °C

Procedure

The title compound is synthesized according to general procedure GP4 starting from 850 mg (2.18 mmol) 4-[3-(6-Amino-pyridin-3-ylethynyl)-2-ethyl-pyridin-4-yl]-2-fluoro-benzoic acid methyl ester (A-45) using 3.3 mL (3.3 mmoL) 1N NaOH in 22 mL THF. The reaction mixture is stirred for 72 h at 65° C. The product is precipitated by addition of water and is collected by filtration. Yield after drying: 747 mg (91%).

Workup

  1. customThe product is precipitated by addition of water
  2. filtrationis collected by filtration
  3. customYield
  4. customafter drying

Sources & evidence

ORD record
ord-8352f6d4fb954c9db67153d1e203a9bf
Source dataset
uspto-grants-2015_07
Patent number
US09090564B2

Reaction notes

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