HCID 86711927, compound → HCID 86711928, compound

HRID 1475236Notes

Reaction equation

HRID 1475236 reaction equation
[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([N+:14]([O-])=O)[CH:9]=2)[N:5]=[C:4]([C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:31])[F:30])=[CH:24][CH:23]=3)[N:18]=2)[N:3]=1>CCO.[Pd]>[CH3:1][C:2]1[N:6]([CH2:7][C:8]2[CH:9]=[C:10]([NH2:14])[CH:11]=[CH:12][CH:13]=2)[N:5]=[C:4]([C:17]2[O:21][N:20]=[C:19]([C:22]3[CH:27]=[CH:26][C:25]([O:28][C:29]([F:32])([F:30])[F:31])=[CH:24][CH:23]=3)[N:18]=2)[N:3]=1

Participants

4

Reactant 1

HCID 86711927HCID 86711927, compound

Product 1

HCID 86711928HCID 86711928, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A mixture of 5-(5-methyl-1-(3-nitrobenzyl)-1H-1,2,4-triazol-3-yl)-3-(4-(trifluoromethoxy)phenyl)-1,2,4-oxadiazole (100 mg, 0.231 mmol) and Pd/C (10% w, 10 mg) in EtOH (10 mL) was stirred at RT for 2 h under hydrogen atmosphere. The reaction mixture was then filtered and concentrated under reduced pressure, and the residue was purified by prep-HPLC (Mobile phase: A=0.1% formic acid/H2O, B=MeCN; Gradient: B=36%-95% in 18 min; Column: XBridge C18, 5 um, 30 mm×150 mm) to give the title compound as a white solid; MS (ES+) C19H13ClF3N5O4S requires: 416. found: 417 (M+H)+; 1H NMR (500 MHz, DMSO-d6) δ ppm 8.31-8.28 (m, 2H), 7.34 (m, 2H), 7.26 (s, 1H), 7.14 (m, 1H), 6.63 (m, 1H), 6.51 (m, 1H), 5.36 (s, 2H), 2.52 (s, 3H).

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationconcentrated under reduced pressure
  3. customthe residue was purified by prep-HPLC (Mobile phase
  4. waitGradient: B=36%-95% in 18 min

Sources & evidence

ORD record
ord-d3c1fcbc12ab4e42885cb798ba2adac0
Source dataset
uspto-grants-2015_04
Patent number
US09018380B2

Reaction notes

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