Hydrochloric Acid → HCID 45381924, compound

HRID 2383349Notes

Reaction equation

HRID 2383349 reaction equation
[C:1]([C:3]1[C:12]2[C:7](=[C:8]([F:15])[C:9]([O:13]C)=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:16]2[S:17][C:18]([C:22]([OH:24])=[O:23])=[C:19]([CH3:21])[N:20]=2)[CH:4]=1)#[N:2].B(Br)(Br)Br.Cl>ClCCl>[C:1]([C:3]1[C:12]2[C:7](=[C:8]([F:15])[C:9]([OH:13])=[CH:10][CH:11]=2)[CH:6]=[C:5]([C:16]2[S:17][C:18]([C:22]([OH:24])=[O:23])=[C:19]([CH3:21])[N:20]=2)[CH:4]=1)#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 25134Boron tribromideHCID 58409500HCID 58409500, compound

Product 1

HCID 45381924HCID 45381924, compoundYield 8.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 2-(4-cyano-8-fluoro-7-methoxynaphthalene-2-yl)-4-methylthiazole-5-carboxylic acid (0.22 g) in dichloromethane (1 mL) was added boron tribromide (1 mol/L dichloromethane solution, 128 μL) under methanol-ice-cooling, and the mixture was stirred at room temperature for 30 minutes, followed by stirring with heating at 40° C. for 2.5 hours. After cooling to room temperature, to the mixture was added 1 mol/L hydrochloric acid. The precipitated crystal was collected by filtration, and dried under reduced pressure at 50° C. to give the title compound (0.018 g).

Workup

  1. temperaturecooling
  2. stirringby stirring
  3. temperaturewith heating at 40° C. for 2.5 hours
  4. temperatureAfter cooling to room temperature, to the mixture
  5. filtrationThe precipitated crystal was collected by filtration
  6. customdried under reduced pressure at 50° C.

Sources & evidence

ORD record
ord-45b445cbcf554971bed3d6438c57ba1f
Source dataset
uspto-grants-2012_09
Patent number
US08263622B2

Reaction notes

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