Tetrahydrofuran → HCID 86295845, compound

HRID 1752617Notes

Reaction equation

HRID 1752617 reaction equation
[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N:9]2[CH2:14][CH2:13][S:12](=[O:16])(=[O:15])[CH2:11][CH2:10]2)=[C:5]2[C:17](=[O:33])[N:18]([CH2:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[C:19](=S)[C:4]2=[CH:3]1.C1COCC1>[Ni].CCO>[CH3:1][N:2]1[C:7](=[O:8])[C:6]([N:9]2[CH2:10][CH2:11][S:12](=[O:16])(=[O:15])[CH2:13][CH2:14]2)=[C:5]2[C:17](=[O:33])[N:18]([CH2:21][CH2:22][C:23]3[CH:32]=[CH:31][C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[N:24]=3)[CH2:19][C:4]2=[CH:3]1

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 90421943HCID 90421943, compound

Product 1

HCID 86295845HCID 86295845, compoundYield 48%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 702EthanolSolvent

Procedure

Raney nickel (0.012 g, 0.207 mmol) was added to s suspension of 5-methyl-7-(1,1-dioxo-thiomorpholin-4-yl)-2-(2-quinolin-2-yl-ethyl)-1,6-dioxo-5H-pyrrolo[3,4-c]pyridine-3-thione (0.1 g, 0.207 mmol, see Example 12.1) in EtOH (5 ml)/THF (5 ml) and the reaction was allowed to stir under an hydrogen atmosphere (pressure of about 35 psi) at r.t. for 16 h. The reaction was filtered through a pad of celite and concentrated. The resulting mixture was purified by preparative HPLC (Waters system, eluent: MeCN/ammonium acetate buffer (gradient: 12:88 to 45:55 over 15 min), column: Boston Analytics, C-18, 10 μm, 10×250 mm) to afford the title compound (45 mg, 48.0% yield).

Workup

  1. filtrationThe reaction was filtered through a pad of celite
  2. concentrationconcentrated
  3. customThe resulting mixture was purified by preparative HPLC (Waters system, eluent: MeCN/ammonium acetate buffer (gradient: 12:88 to 45:55 over 15 min), column: Boston Analytics, C-18, 10 μm, 10×250 mm)

Sources & evidence

ORD record
ord-f823fe7ce6ee474fa8441765bd4a33fd
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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