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

HRID 1771841Notes

Reaction equation

HRID 1771841 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, 1 H), 7.72 (d, J=8.0 Hz, 1 H), 6.86 (t, J=1.8 Hz, 1 H), 6.52 (dd, J=3.8, 1.5 Hz, 1 H), 6.12 (dd, J=3.8, 2.5 Hz, 1 H), 4.96 (s, 2 H), 4.07 (t, J=5.8 Hz, 2 H), 3.74 (s, 3 H), 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-efef072b16c44c18986ae7c64a868832
Source dataset
uspto-grants-2016_02
Patent number
US09249142B2

Reaction notes

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