Hydrochloric Acid → N-Hydroxy-2-(1H-indol-3-ylacetyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide

HRID 2036871Notes

Reaction equation

HRID 2036871 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]([CH2:10][C:11]([N:13]2[CH2:22][CH2:21][C:20]3[C:15](=[CH:16][C:17]([C:23]([NH:25][O:26]C4CCCCO4)=[O:24])=[CH:18][CH:19]=3)[CH2:14]2)=[O:12])=[CH:2]1.Cl>CO>[OH:26][NH:25][C:23]([C:17]1[CH:16]=[C:15]2[C:20]([CH2:21][CH2:22][N:13]([C:11](=[O:12])[CH2:10][C:3]3[C:4]4[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=4)[NH:1][CH:2]=3)[CH2:14]2)=[CH:19][CH:18]=1)=[O:24]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86656607HCID 86656607, compound

Product 1

HCID 44229353N-Hydroxy-2-(1H-indol-3-ylacetyl)-1,2,3,4-tetrahydroisoquinoline-7-carboxamideYield 63.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 180 mg 2-(1H-indol-3-ylacetyl)-N-(tetrahydro-2H-pyran-2-yloxy)-1,2,3,4-tetrahydroisoquinoline-7-carboxamide, 6 ml methanol and 6 ml 0.1 N aqueous hydrochloric acid are stirred at ambient temperature overnight. The reaction mixture is evaporated and the residue is dissolved in a mixture of acetonitrile and water and lyophilized. 92 mg of the title compound are obtained. MH+=350.0

Workup

  1. customThe reaction mixture is evaporated
  2. dissolutionthe residue is dissolved in a mixture of acetonitrile and water

Sources & evidence

ORD record
ord-94c189c322b34180bbd0b7e10befd700
Source dataset
uspto-grants-2013_11
Patent number
US08575193B2

Reaction notes

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