HCID 68772019, compound → HCID 11536065, compound

HRID 1172349Notes

Reaction equation

HRID 1172349 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([NH2:15])[CH2:13][CH:12]=[CH:11][CH2:10]1>CO.Cl.[Pd]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C@H:9]1[C@H:14]([NH2:15])[CH2:13][CH2:12][CH2:11][CH2:10]1

Participants

5

Reactant 1

HCID 68772019HCID 68772019, compound

Product 1

HCID 11536065HCID 11536065, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 2B (100 mg, 0.041 mmol) in 1:1 in methanol (2 mL), two drops of concentrated HCl and 10% palladium on carbon (10 mg) were added. The solution was purged with nitrogen and subjected to an atmosphere of H2 over a twelve hour period. The solution was filtered through Celite and concentrated to give the title compound. 1H NMR (300 MHz, C5D5N) δ ppm 7.26 (s, 1H), 7.17-7.19 (m, 2H), 3.96-3.99 (m, 1H), 3.65-3.69 (m, 1H), 2.94-2.96 (m, 1H), 2.06-2.08 (m, 1H), 1.80-1.83 (m, 1H), 1.58-1.67 (m, 2H), 1.25-1.39 (m, 3H). MS (ESI+) m/z 245 (M+H)+.

Workup

  1. customThe solution was purged with nitrogen
  2. waitsubjected to an atmosphere of H2 over a twelve hour period
  3. filtrationThe solution was filtered through Celite
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-6c6c88643db64838b77d4a393bd1b040
Source dataset
uspto-grants-2010_11
Patent number
US07834012B2

Reaction notes

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