N2-(2-phenylethyl)-N7-(tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroisoquinoline-2,7(1H)-dicarboxamide → N7-Hydroxy-N2-(2-phenylethyl)-3,4-dihydroisoquinoline-2,7(1H)-dicarboxamide

HRID 2036875Notes

Reaction equation

HRID 2036875 reaction equation
[C:1]1([CH2:7][CH2:8][NH:9][C:10]([N:12]2[CH2:21][CH2:20][C:19]3[C:14](=[CH:15][C:16]([C:22]([NH:24][O:25]C4CCCCO4)=[O:23])=[CH:17][CH:18]=3)[CH2:13]2)=[O:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1>CO.Cl>[OH:25][NH:24][C:22]([C:16]1[CH:15]=[C:14]2[C:19]([CH2:20][CH2:21][N:12]([C:10]([NH:9][CH2:8][CH2:7][C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[O:11])[CH2:13]2)=[CH:18][CH:17]=1)=[O:23]

Participants

4

Reactant 1

HCID 86656613N2-(2-phenylethyl)-N7-(tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroisoquinoline-2,7(1H)-dicarboxamide

Product 1

HCID 44229427N7-Hydroxy-N2-(2-phenylethyl)-3,4-dihydroisoquinoline-2,7(1H)-dicarboxamideYield 61.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 200 mg N2-(2-phenylethyl)-N7-(tetrahydro-2H-pyran-2-yloxy)-3,4-dihydroisoquinoline-2,7(1H)-dicarboxamide in 6 ml methanol and 6 ml 0.1 N aqueous hydrochloric acid is stirred overnight at ambient temperature. Subsequently, the reaction mixture is evaporated. The residue is dissolved in a mixture of water and acetonitrile and lyophilized. The crude product is further purified by silica gel flash chromatography. 98 mg of the title compound are obtained. MH+=340.1

Workup

  1. customSubsequently, the reaction mixture is evaporated
  2. dissolutionThe residue is dissolved in a mixture of water and acetonitrile
  3. customThe crude product is further purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-8687455019444d089911a9a9c5faf2d1
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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