Hydrochloric Acid → HCID 117737585, compound

HRID 1750884Notes

Reaction equation

HRID 1750884 reaction equation
Cl.[Cl:2][C:3]1[CH:22]=[CH:21][C:20]([NH:23][C:24]2[C:33]3[C:28](=[C:29]([N+:35]([O-])=O)[C:30]([CH3:34])=[CH:31][CH:32]=3)[CH:27]=[CH:26][N:25]=2)=[CH:19][C:4]=1[CH2:5][N:6]1[CH2:11][CH2:10][N:9]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:8][CH2:7]1>[Fe].C(O)C.O>[NH2:35][C:29]1[C:30]([CH3:34])=[CH:31][CH:32]=[C:33]2[C:28]=1[CH:27]=[CH:26][N:25]=[C:24]2[NH:23][C:20]1[CH:21]=[CH:22][C:3]([Cl:2])=[C:4]([CH:19]=1)[CH2:5][N:6]1[CH2:7][CH2:8][N:9]([C:12]([O:14][C:15]([CH3:16])([CH3:17])[CH3:18])=[O:13])[CH2:10][CH2:11]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 89655676HCID 89655676, compound

Product 1

HCID 117737585HCID 117737585, compoundYield 72%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 19096565Water ethanolSolvent

Procedure

Iron (257 mg, 4.145 mmol) and concentrated hydrochloric acid (0.03 mL) were added to ethanol/water (10 mL/10 mL), and refluxed for 1 hour. The mixed reaction solution was added with tert-butyl 4-(2-chloro-5-((6-methyl-5-nitroisoquinolin-1-yl)amino)benzyl)piperazine-1-carboxylate (424.5 mg, 0.829 mmol) obtained in <Step 3> above, and refluxed for 3 hours. The reaction mixture was filtered a Celite pad under reduced pressure, and washed with ethanol and chloroform/2-propanol=3/1 (v/v). The filtrate obtained was distilled under reduced pressure, and dissolved in chloroform/2-propanol=3/1 (v/v). The organic layer was washed with an aqueous solution of sodium bicarbonate and brine. The obtained organic layer was dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrated compound was purified using silica gel chromatography (ethyl acetate:hexane=1:3→1:2 (v/v)) to obtain the title compound (286 mg, 72%).

Workup

  1. temperaturerefluxed for 1 hour
  2. customThe mixed reaction solution
  3. customobtained in <Step 3> above
  4. temperaturerefluxed for 3 hours
  5. filtrationThe reaction mixture was filtered a Celite pad under reduced pressure
  6. washwashed with ethanol and chloroform/2-propanol=3/1 (v/v)
  7. customThe filtrate obtained
  8. distillationwas distilled under reduced pressure
  9. dissolutiondissolved in chloroform/2-propanol=3/1 (v/v)
  10. washThe organic layer was washed with an aqueous solution of sodium bicarbonate and brine
  11. dry with materialThe obtained organic layer was dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. concentrationconcentrated under reduced pressure
  14. customThe concentrated compound was purified

Sources & evidence

ORD record
ord-3a42d34005494c918532e9b19579386e
Source dataset
uspto-grants-2015_10
Patent number
US09156852B2

Reaction notes

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