Hydrochloric Acid → HCID 22131463, compound

HRID 1857679Notes

Reaction equation

HRID 1857679 reaction equation
[N+:1]([CH:4]=[CH:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[C:16]([C:21]3[CH:26]=[CH:25][C:24]([C:27]([F:30])([F:29])[F:28])=[CH:23][CH:22]=3)=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1)([O-])=O.[ClH:31]>[Pd].C(O)C>[ClH:31].[NH2:1][CH2:4][CH2:5][C:6]1[CH:7]=[C:8]([NH:12][C:13]([C:15]2[C:16]([C:21]3[CH:22]=[CH:23][C:24]([C:27]([F:28])([F:29])[F:30])=[CH:25][CH:26]=3)=[CH:17][CH:18]=[CH:19][CH:20]=2)=[O:14])[CH:9]=[CH:10][CH:11]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54467924HCID 54467924, compound

Product 1

HCID 22131463HCID 22131463, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

A Parr® hydrogenation flask was charged with the title product of Example 2 (1.90 g, 4.61 mmol), 10% Pd/C (0.58 g), 95% ethanol (20 mL), and conc. HCl (0.96 mL, 12 mmol). The mixture was hydrogenated, under hydrogen at 276 kPa (40 psi), for 19 hours. The catalyst was removed by filtration through Celite®, and the filtrate was concentrated to provide an oily, yellow-white solid, which was 85% pure by HPLC analysis. A portion of this material was purified as its free base (i.e., the HCl salt was dissolved in methanol, treated with one molar equivalent of K2CO3 filtered and concentrated) by silica gel chromatography, eluting with 500:50:1 CH2Cl2 -methanol-NH4OH, providing the title product as a white solid which was homogenous by HPLC analysis.

Workup

  1. customThe catalyst was removed by filtration through Celite®
  2. concentrationthe filtrate was concentrated
  3. customto provide an oily, yellow-white solid, which
  4. customA portion of this material was purified as its free base (i.e.
  5. dissolutionthe HCl salt was dissolved in methanol
  6. additiontreated with one molar equivalent of K2CO3
  7. filtrationfiltered
  8. concentrationconcentrated) by silica gel chromatography
  9. washeluting with 500:50:1 CH2Cl2 -methanol-NH4OH

Sources & evidence

ORD record
ord-22f9aa6efa994d74b79253fe652d98df
Source dataset
uspto-grants-2000_11
Patent number
US06147214

Reaction notes

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