Hydrochloric Acid → HCID 66995423, compound

HRID 1160833Notes

Reaction equation

HRID 1160833 reaction equation
[OH-].[Na+].CO.[NH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:22][C:21]([C:23]([O:25]C)=[O:24])=[CH:20][CH:19]=3)=[CH:14][C:13]=2[C:27]#[N:28])[CH:9]=[CH:10][CH:11]=1.Cl>O1CCCC1>[NH2:5][C:6]1[CH:7]=[C:8]([C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:22][C:21]([C:23]([OH:25])=[O:24])=[CH:20][CH:19]=3)=[CH:14][C:13]=2[C:27]#[N:28])[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 14798Sodium HydroxideHCID 66995115HCID 66995115, compound

Product 1

HCID 66995423HCID 66995423, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

0.2 ml of aqueous 1 M sodium hydroxide solution was added to a methanol (0.25 ml)/tetrahydrofuran (0.25 ml) solution of methyl 5-(3′-amino-2-cyanobiphenyl-4-yl)thiophene-2-carboxylate, followed by stirring overnight at 60° C. 1 M hydrochloric acid was added to the reaction liquid to make it acidic, and the solvent was evaporated under reduced pressure. The residue was purified by HPLC [elution through column: SunFire (registered trademark) C18 5 μm, 19 mm×100 mm, solvent: MeOH/aqueous 0.1% formic acid solution 10/90 for 1 minute, ratio change to 95/5, taking 8 minutes, and further elution with 95/5 for 3 minutes, flow rate: 25 mL/min), thereby obtaining 2.5 mg of 5-(3′-amino-2-cyanobiphenyl-4-yl)thiophene-2-carboxylic acid.

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by HPLC [
  3. washelution through column
  4. waitSunFire (registered trademark) C18 5 μm, 19 mm×100 mm, solvent: MeOH/aqueous 0.1% formic acid solution 10/90 for 1 minute
  5. waitratio change to 95/5, taking 8 minutes
  6. washfurther elution with 95/5 for 3 minutes

Sources & evidence

ORD record
ord-4748aa7dda504018853c5870084af86d
Source dataset
uspto-grants-2010_10
Patent number
US07816558B2

Reaction notes

Loading…