Hydrochloric Acid → HCID 71278643, compound

HRID 1749706Notes

Reaction equation

HRID 1749706 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:21][N:22]([CH3:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][N:31](C)[C:32](=O)OC(C)(C)C)=[C:19]([OH:41])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.Cl>C(Cl)Cl.O1CCOCC1>[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3](/[CH:10]=[C:11]2\[O:12][C:13]3[C:20]([CH2:21][N:22]([CH3:40])[CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][NH:31][CH3:32])=[C:19]([OH:41])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 86681909HCID 86681909, compound

Product 1

HCID 71278643HCID 71278643, compoundYield 60.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-8-[({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)(methyl)amino]octyl(methyl)carbamate (0.020 g, 0.036 mmol) in methylene chloride (2.0 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (2.0 mL), and then the mixture was stirred at room temperature for 1 hour. The solvent was evaporated under reduced pressure, and then the residue was added with triethylamine and thereby made basic. Then, the mixture was azeotroped with toluene, and then the residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10)) to obtain (Z)-2-[(1H-indol-3-yl)methylene]-6-hydroxy-7-({methyl[8-(methylamino)octyl]amino}methyl)benzofuran-3(2H)-one (0.010 g, 60%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. additionthe residue was added with triethylamine
  3. customThen, the mixture was azeotroped with toluene
  4. washthe residue was subjected to silica gel column chromatography (aminopropyl silica was used, eluted with chloroform/methanol (90:10))

Sources & evidence

ORD record
ord-e2b936cfe78240768efb8067c0d4503f
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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