HCID 90421601, compound → HCID 117628772, compound

HRID 1752598Notes

Reaction equation

HRID 1752598 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]2[C:10](=[O:26])[N:11]([CH2:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[C:12](=[O:13])[C:3]=12>C(O)(=O)C.[Cl-].[Na+].O.[Zn]>[Cl:1][C:2]1[C:7](=[O:8])[N:6]([CH3:9])[CH:5]=[C:4]2[C:10](=[O:26])[N:11]([CH2:14][CH2:15][C:16]3[CH:25]=[CH:24][C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[N:17]=3)[CH:12]([OH:13])[C:3]=12

Participants

5

Reactant 1

HCID 90421601HCID 90421601, compound

Product 1

HCID 117628772HCID 117628772, compoundYield 139.2%

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 176Acetic AcidSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Zinc (0.44 g, 6.8 mmol) was added to a solution of 7-chloro-5-methyl-2-(2-quinolin-2-yl-ethyl)-5H-pyrrolo[3,4-c]pyridine-1,3,6-trione (1 g, 2.72 mmol, see Example c1)) in acetic acid (10 ml) and the reaction was stirred for 3 h under reflux. The reaction was cooled to r.t. and brine (20 ml) was added. The aqueous layer was extracted with THF (3×25 ml) and the combined organic phase was concentrated to dryness. The mixture was diluted with THF (30 ml)/MeOH (5 ml), filtered through a pad of silica gel and concentrated to give crude product (1.4 g 139% yield), which was used in the next steps without further purification.

Workup

  1. temperatureunder reflux
  2. extractionThe aqueous layer was extracted with THF (3×25 ml)
  3. concentrationthe combined organic phase was concentrated to dryness
  4. additionThe mixture was diluted with THF (30 ml)/MeOH (5 ml)
  5. filtrationfiltered through a pad of silica gel
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-bb4076c516a7492aa58272123e686b1c
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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