HCID 86656610, compound → N-Hydroxy-2-(tetrahydrofuran-3-ylcarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

HRID 2036873Notes

Reaction equation

HRID 2036873 reaction equation
[O:1]1[CH2:5][CH2:4][CH:3]([C:6]([N:8]2[CH2:17][CH2:16][C:15]3[C:10](=[CH:11][C:12]([C:18]([NH:20][O:21]C4CCCCO4)=[O:19])=[CH:13][CH:14]=3)[CH2:9]2)=[O:7])[CH2:2]1>CO.Cl>[OH:21][NH:20][C:18]([C:12]1[CH:11]=[C:10]2[C:15]([CH2:16][CH2:17][N:8]([C:6]([CH:3]3[CH2:4][CH2:5][O:1][CH2:2]3)=[O:7])[CH2:9]2)=[CH:14][CH:13]=1)=[O:19]

Participants

4

Reactant 1

HCID 86656610HCID 86656610, compound

Product 1

HCID 44229425N-Hydroxy-2-(tetrahydrofuran-3-ylcarbonyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamideYield 23.4%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Procedure

A mixture of 110 mg 2-(tetrahydrofuran-3-ylcarbonyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide 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 purified by silica gel flash chromatography. 20 mg of the title compound are obtained as colorless solid. MH+=291.1

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 purified by silica gel flash chromatography

Sources & evidence

ORD record
ord-8eccd862d6ac4af2b676a2054fea0eab
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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