Pyridine → 7-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amide

HRID 269994Notes

Reaction equation

HRID 269994 reaction equation
Br[C:2]1[CH:11]=[C:10]2[C:5]([CH:6]=[CH:7][N:8]=[CH:9]2)=[CH:4][CH:3]=1.[C:12]([O-])(O)=O.[Na+].C(OC([NH:24][CH2:25][CH2:26][NH2:27])=O)(C)(C)C.N1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.[SH:34]([O:37]Cl)(=O)=[O:35]>C(Cl)Cl>[NH2:27][CH2:26][CH2:25][NH:24][S:34]([C:4]1[C:5]2[CH:6]=[CH:7][N:8]=[CH:9][C:10]=2[CH:11]=[C:2]([C:29]2[CH:12]=[CH:33][CH:32]=[CH:31][CH:30]=2)[CH:3]=1)(=[O:37])=[O:35]

Participants

7

Reactant 5

HCID 1049PyridineHCID 187201N-BOC-ethylenediamineHCID 516892Sodium BicarbonateHCID 122574417-BromoisoquinolineHCID 178527254HCID 178527254, compound

Product 1

HCID 112903567-Phenyl-isoquinoline-5-sulfonic acid (2-amino-ethyl)-amideYield 50%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
155 °C

Procedure

A mixture of 7-bromoisoquinoline (6.5 g, 31.24 mmol) in HSO3Cl (60 mL) is heated to 155° C. with stirring under N2 overnight, and then cooled to room temperature and slowly poured into ice water. After neutralizing with NaHCO3 at 0° C., sulfonyl chloride is extracted with methylene chloride. The organic layer is dried over Na2SO4 and concentrated to 100 mL and dropped to a solution of N-t-butoxycarbonylethylene diamine (5.01 g, 31.24 mmol) in pyridine (2.54 mL, 31.24 mmol) and CH2Cl2 (120 mL). After stirring overnight, the mixture is concentrated, and the residue is dissolved in EtOAc, which is washed with citric acid solution (50%) and brine. The crude material is purified by chromatography over silica gel (gradient 20% hexane in EtOAc) to give 6.50 g (50% yield) of desired product

Workup

  1. temperaturecooled to room temperature
  2. extractionsulfonyl chloride is extracted with methylene chloride
  3. dry with materialThe organic layer is dried over Na2SO4
  4. concentrationconcentrated to 100 mL
  5. stirringAfter stirring overnight
  6. concentrationthe mixture is concentrated
  7. dissolutionthe residue is dissolved in EtOAc
  8. washwhich is washed with citric acid solution (50%) and brine
  9. customThe crude material is purified by chromatography over silica gel (gradient 20% hexane in EtOAc)

Sources & evidence

ORD record
ord-fa0fb79887d646c5b27ca47b1d14f14a
Source dataset
uspto-grants-2008_11
Patent number
US07449477B2

Reaction notes

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