Hydrochloric Acid → HCID 68162163, compound

HRID 2041762Notes

Reaction equation

HRID 2041762 reaction equation
[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]3)=[CH:11][CH:12]=2)[CH:7]([NH:20][C:21]2[N:26]=[CH:25][C:24]([C:27]([OH:29])=[O:28])=[CH:23][CH:22]=2)[CH2:6][CH:5]1[CH3:30])(=[O:3])[CH3:2].Cl.[CH3:32]O>>[C:1]([N:4]1[C:13]2[C:8](=[CH:9][C:10]([N:14]3[CH:18]=[C:17]([CH3:19])[N:16]=[CH:15]3)=[CH:11][CH:12]=2)[C@H:7]([NH:20][C:21]2[N:26]=[CH:25][C:24]([C:27]([O:29][CH3:32])=[O:28])=[CH:23][CH:22]=2)[CH2:6][C@@H:5]1[CH3:30])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 313Hydrochloric Acid2×HCID 887MethanolHCID 67205323HCID 67205323, compound

Product 1

HCID 68162163HCID 68162163, compoundYield 29%

Procedure

A solution of 6-{[1-acetyl-2-methyl-6-(4-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinyl]amino}-3-pyridinecarboxylic acid (for a preparation see example 143) (40 mg, 0.099 mmol) in dry methanol (2 mL) was treated at room temperature with HCl (4M in 1,4-dioxane, 200 μl, 0.800 mmol) and the resulting mixture was stirred at this temperature for one hour. Another portion of HCl (4M in 1,4-dioxane, 200 μl, 0.800 mmol) was added and the mixture was refluxed for 1 hour then cooled to room temperature and concentrated in vacuo. The residue was purified using MDAP (modifier: ammonium formate) to give methyl 6-{[(cis)-1-acetyl-2-methyl-6-(4-methyl-1H-imidazol-1-yl)-1,2,3,4-tetrahydro-4-quinolinyl]amino}-3-pyridinecarboxylate (12 mg, 0.029 mmol, 29%) as a white solid.

Workup

  1. temperaturethe mixture was refluxed for 1 hour
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified

Sources & evidence

ORD record
ord-9cf7ea66d52d49f595765188a915e0f3
Source dataset
uspto-grants-2013_11
Patent number
US08580957B2

Reaction notes

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