HCID 78210284, compound → HCID 86295636, compound

HRID 1752609Notes

Reaction equation

HRID 1752609 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[C:5]2[C:15](=O)[N:16]([CH2:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[C:17](=[O:18])[C:4]2=[CH:3]1>C(O)(=O)C.[Zn]>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[C:5]2[CH2:15][N:16]([CH2:19][CH2:20][C:21]3[CH:30]=[CH:29][C:28]4[C:23](=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:22]=3)[C:17](=[O:18])[C:4]2=[CH:3]1

Participants

4

Reactant 1

HCID 78210284HCID 78210284, compound

Product 1

HCID 86295636HCID 86295636, compoundYield 6.1%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 176Acetic AcidSolvent

Procedure

Zinc (0.375 g, 5.74 mmol) was added to a solution of 5-methyl-7-morpholin-4-yl-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trione (0.8 g, 1.91 mmol, see Example 1) in acetic acid (15 ml) and the reaction was stirred for 8 h under reflux. The solvent was removed and the resulting mixture was purified via preparative HPLC (Waters system, eluent: MeCN/ammonium acetate buffer (gradient: 10:90 to 80:20 over 20 min), column: Hanbon Benetnach C18, 10 μm, 21.2×250 mm) to afford the title compound (47 mg, 6% yield).

Workup

  1. temperatureunder reflux
  2. customThe solvent was removed
  3. customthe resulting mixture was purified via preparative HPLC (Waters system, eluent: MeCN/ammonium acetate buffer (gradient: 10:90 to 80:20 over 20 min), column: Hanbon Benetnach C18, 10 μm, 21.2×250 mm)

Sources & evidence

ORD record
ord-89ae0cb9396844b9ba524a95875ae714
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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