Ethanol → HCID 86295842, compound

HRID 1752613Notes

Reaction equation

HRID 1752613 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:19])[NH:16][C:17](=S)[C:4]2=[C:3]1CCC1C=CC2C(=CC=CC=2)N=1.[CH2:32]1[CH2:36]O[CH2:34][CH2:33]1.[CH3:37][CH2:38]O>[Ni]>[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:19])[N:16]([CH2:34][CH2:33][C:32]3[CH:36]=[CH:37][C:38]4[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=4)[N:2]=3)[CH2:17][C:4]2=[CH:3]1

Participants

5

Reactant 3

HCID 702EthanolHCID 8028TetrahydrofuranHCID 90421930HCID 90421930, compound

Product 1

HCID 86295842HCID 86295842, compoundYield 24.36%

Reagents, catalysts & solvents 1

HCID 935NickelCatalyst

Procedure

Nickel (7.56 mg, 0.129 mmol) was added rapidly to a mixture of 5-methyl-7-morpholin-4-yl-(2-quinolin-2-yl-ethyl)-1,6-dioxo-5H-pyrrolo[3,4-c]pyridine-3-thione (0.56 g, 1.289 mmol, see Example 9.1) in EtOH (20 ml)/THF (5 ml). The mixture was allowed to stir under a hydrogen atmosphere (at a pressure of about 35 psi) at r.t. for about 16 h. The solvent was removed and the resulting mixture was purified via preparative HPLC (System: Isco Combi Flash Companion XL, eluent: MeCN/ammonium acetate buffer (gradient: 0:100 to 60:40 over 20 min), column: C-18, 21.2×250 mm) to afford the title compound (127 mg, 24.36% yield).

Workup

  1. customThe solvent was removed
  2. customthe resulting mixture was purified via preparative HPLC (System: Isco Combi Flash Companion XL, eluent: MeCN/ammonium acetate buffer (gradient: 0:100 to 60:40 over 20 min), column: C-18, 21.2×250 mm)

Sources & evidence

ORD record
ord-ad5dad9c524541809e4a6c4be9edb645
Source dataset
uspto-grants-2015_10
Patent number
US09163019B2

Reaction notes

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