Lithium Hydroxide → HCID 90077540, compound

HRID 2203254Notes

Reaction equation

HRID 2203254 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([O:14]CC)=[O:13])=[C:5]2[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[CH:19]=1.[OH-].[Li+]>CO.O1CCCC1.O>[Cl:1][C:2]1[N:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[CH:7][C:6]([C:12]([OH:14])=[O:13])=[C:5]2[NH:17][C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:25])([F:26])[F:27])[CH:19]=1

Participants

6

Reactant 2

HCID 3939Lithium HydroxideHCID 86714218HCID 86714218, compound

Product 1

HCID 90077540HCID 90077540, compoundYield 97.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

ethyl 6-chloro-4-((3-(trifluoromethyl)phenyl)amino)-1,5-naphthyridine-3-carboxylate (3.95 g, 10 mmol) was dissolved in 50 mL methanol and 50 mL tetrahydrofuran. To the resulting mixture was added dropwise a solution of lithium hydroxide (1.26 g, 30 mmol) in water (50 mL). After the completion of the dropwise addition, the resulting mixture is reacted at room temperature for 4 hrs. The reaction was concentrated, and 200 mL water was added. The resulting mixture was adjusted with hydrochloric acid to pH=3. The solid was separated, and dried in vacuum to obtain a yellow solid (3.6 g).

Workup

  1. additionAfter the completion of the dropwise addition
  2. customthe resulting mixture is reacted at room temperature for 4 hrs
  3. concentrationThe reaction was concentrated
  4. addition200 mL water was added
  5. customThe solid was separated
  6. customdried in vacuum

Sources & evidence

ORD record
ord-ff5c08cc868c4e1fa1801dd0cecc1d07
Source dataset
uspto-grants-2016_06
Patent number
US09365572B2

Reaction notes

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