Acetic Acid → N-Hydroxy-2-[(1-methyl-1H-pyrrol-2-yl)carbonyl]-1,2,3,4-tetrahydro-6-isoquinolinecarboxamide

HRID 1261732Notes

Reaction equation

HRID 1261732 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][CH:4]=[C:3]1[C:7]([N:9]1[CH2:18][CH2:17][C:16]2[C:11](=[CH:12][CH:13]=[C:14]([C:19]([O:21]C)=O)[CH:15]=2)[CH2:10]1)=[O:8].[K].[NH2:24][OH:25].C(O)(=O)C>CO>[OH:25][NH:24][C:19]([C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[CH2:10][N:9]([C:7]([C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][CH:4]=1)=[O:8])[CH2:18][CH2:17]2)=[O:21]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 58147289HCID 58147289, compoundHCID 86662665HCID 86662665, compound

Product 1

HCID 49831258N-Hydroxy-2-[(1-methyl-1H-pyrrol-2-yl)carbonyl]-1,2,3,4-tetrahydro-6-isoquinolinecarboxamideYield 16.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 2-(1-methyl-1H-pyrrole-2-carbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxylate in a vial was dissolved in MeOH (1 mL) and hydroxylamine potassium salt (0.682 mL, 1.2 mmol; 1.76 M in MeOH) was added. The solution was shaken at rt for 2 h before acetic acid (0.0682 mL, 1.2 mmol) was added to neutralize the reaction. The solvent was then completely evaporated and to the residue was added DMSO (1.2 mL). After filtration, the solution was purified by prep-HPLC to yield N-hydroxy-2-(1-methyl-1H-pyrrole-2-carbonyl)-1,2,3,4-tetrahydroisoquinoline-6-carboxamide (0.0073 g, 16.2%). LC-MS: (AA) ES+ 301; 1H NMR (Methanol-d4, 400 MHz) δ 7.87 (d, J=8.0 Hz, 1H), 7.72 (d, J=8.0 Hz, 1H), 6.86 (t, J=1.8 Hz, 1H), 6.52 (dd, J=3.8, 1.5 Hz, 1H), 6.12 (dd, J=3.8, 2.5 Hz, 1H), 4.96 (s, 2H), 4.07 (t, J=5.8 Hz, 2H), 3.74 (s, 3H), 3.11 (t, J=6.0 Hz, 2H).

Workup

  1. additionwas added
  2. customthe reaction
  3. customThe solvent was then completely evaporated and to the residue
  4. additionwas added DMSO (1.2 mL)
  5. filtrationAfter filtration
  6. customthe solution was purified by prep-HPLC

Sources & evidence

ORD record
ord-a176443311154ad988289269da25ffdf
Source dataset
uspto-grants-2013_06
Patent number
US08471026B2

Reaction notes

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