Hydrochloric Acid → HCID 60155621, compound

HRID 1749832Notes

Reaction equation

HRID 1749832 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]4[CH2:28][CH2:27][CH2:26][N:25](C(OC(C)(C)C)=O)[CH2:24][CH2:23]4)=[C:19]([OH:36])[CH:18]=[CH:17][C:14]=3[C:15]\2=[O:16])=[CH:2]1.Cl>C(Cl)Cl.O1CCOCC1>[N:22]1([CH2:21][C:20]2[C:13]3[O:12]/[C:11](=[CH:10]\[C:3]4[C:4]5[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=5)[NH:1][CH:2]=4)/[C:15](=[O:16])[C:14]=3[CH:17]=[CH:18][C:19]=2[OH:36])[CH2:28][CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 60155787HCID 60155787, compound

Product 1

HCID 60155621HCID 60155621, compoundYield 75.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution of tert-butyl (Z)-4-({2-[(1H-indol-3-yl)methylene]-6-hydroxy-3-oxo-2,3-dihydrobenzofuran-7-yl}methyl)-1,4-diazepane-1-carboxylate (0.141 g, 0.288 mmol) in methylene chloride (1.5 mL) was added with a 4 M solution of hydrogen chloride in 1,4-dioxane (1.5 mL) at room temperature, and the mixture was stirred for 2 hours. The reaction mixture was concentrated, the resulting residue was added with saturated aqueous sodium hydrogencarbonate, and the mixture was extracted with chloroform. The organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated, and the resulting solid was washed with methylene chloride to obtain (Z)-7-[(1,4-diazepan-1-yl)methyl]-2-[(1H-indol-3-yl)methylene]-6-hydroxybenzofuran-3(2H)-one (0.0843 g, 75%).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. additionthe resulting residue was added with saturated aqueous sodium hydrogencarbonate
  3. extractionthe mixture was extracted with chloroform
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. washthe resulting solid was washed with methylene chloride

Sources & evidence

ORD record
ord-8e54f493d2024261811b74a1ced0c0b3
Source dataset
uspto-grants-2015_10
Patent number
US09156827B2

Reaction notes

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