Ethanol → HCID 67402096, compound

HRID 1186308Notes

Reaction equation

HRID 1186308 reaction equation
[F:1][C:2]([F:39])([F:38])[CH:3]([CH:22]1[CH2:27][CH2:26][N:25](C(OCC2C=CC=CC=2)=O)[CH2:24][CH2:23]1)[O:4][C:5]1[C:6]([NH:15][S:16]([CH2:19][CH2:20][CH3:21])(=[O:18])=[O:17])=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2.C(O)C>O1CCCC1.[Pd]>[F:39][C:2]([F:1])([F:38])[CH:3]([CH:22]1[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]1)[O:4][C:5]1[C:6]([NH:15][S:16]([CH2:19][CH2:20][CH3:21])(=[O:18])=[O:17])=[N:7][C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 2

HCID 702EthanolHCID 67402998HCID 67402998, compound

Product 1

HCID 67402096HCID 67402096, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalyst2×HCID 8028TetrahydrofuranSolvent2×

Procedure

Ten percent palladium/carbon (15.0 mg) was suspended in tetrahydrofuran (1.0 mL). To this, a tetrahydrofuran solution (2.0 mL) of N-{3-[2,2,2-trifluoro-1-(1-benzyloxycarbonylpiperidin-4-yl)ethoxy]quinoxalin-2-yl}propane-1-sulfonamide (150 mg, 0.245 mmol) was added and the mixture was stirred under hydrogen stream at room temperature for 3 days. To the reaction mixture, 10% palladium/carbon (15.0 mg) and ethanol (2.0 mL) were added and the mixture was stirred under hydrogen stream at room temperature for 8 hours. The reaction mixture was filtered through Celite and the solvent was evaporated off under reduced pressure. The residue was purified by preparative thin-layer chromatography (chloroform/methanol=9/1) to give Compound 327 (38.7 mg, yield: 37%).

Workup

  1. stirringthe mixture was stirred under hydrogen stream at room temperature for 8 hours
  2. filtrationThe reaction mixture was filtered through Celite
  3. customthe solvent was evaporated off under reduced pressure
  4. customThe residue was purified by preparative thin-layer chromatography (chloroform/methanol=9/1)

Sources & evidence

ORD record
ord-6e8f153ecf374b2b9103726c8ee42aab
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Reaction notes

Loading…