Water → HCID 57656428, compound

HRID 911582Notes

Reaction equation

HRID 911582 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]2[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][S:9][C:5]=2[CH:4]=1)#[N:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>C1COCC1>[NH2:2][CH2:1][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=3)=[CH:8][S:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962Water2×HCID 14798Sodium HydroxideHCID 21226445Aluminium lithium hydrideHCID 66706909HCID 66706909, compound

Product 1

HCID 57656428HCID 57656428, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Dissolve 6-cyano-3-phenylbenzothiophene (0.27 g, 1.16 mmol) in anhydrous THF (6 mL) and add lithium aluminum hydride (3.45 mL, 1M solution in THF) at 0° C. After 2 h, add water (0.86 mL), 2N aqueous NaOH (0.86 mL) and water (1.24 mL). Filter off the solids and evaporate the residue. Purify by prep HPLC (Zorbax SB-Phenyl column 21.2×250 mm, 5% to 50% acetonitrile in 0.1% TFA-water solution) and obtain the free base by SCX chromatography to give the title compound that is used without further purification (187 mg, 68%). MS (ES+) m/z: 223 (M-NH2)+.

Workup

  1. filtrationFilter off the solids
  2. customevaporate the residue
  3. customPurify by prep HPLC (Zorbax SB-Phenyl column 21.2×250 mm, 5% to 50% acetonitrile in 0.1% TFA-water solution)
  4. customobtain the free base by SCX chromatography

Sources & evidence

ORD record
ord-c2987bcb99e743f5b1979c52667af481
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Reaction notes

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