HCID 89511757, compound → HCID 68195173, compound

HRID 710597Notes

Reaction equation

HRID 710597 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH2:9][CH:8]([N:13]1[CH2:17][CH2:16][CH2:15][CH2:14]1)[CH2:7]2)([O-])=O>CO.[Pd]>[N:13]1([CH:8]2[CH2:7][C:6]3[C:10](=[CH:11][CH:12]=[C:4]([NH2:1])[CH:5]=3)[CH2:9]2)[CH2:17][CH2:16][CH2:15][CH2:14]1

Participants

4

Reactant 1

HCID 89511757HCID 89511757, compound

Product 1

HCID 68195173HCID 68195173, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a solution of Example 55B (7.25 g, 31.2 mmol) in 156 mL of methanol was added palladium on carbon (10% wt) (7.25 g, 6.81 mmol). The reaction mixture was evacuated and backfilled with nitrogen three times then evacuated and backfilled with hydrogen. The mixture was then allowed to stirred under H2 (1 atm, balloon) at ambient temperature overnight. The mixture was filtered through a celite pad then concentrated and the crude product was recrystallized in ethyl acetate/hexane mixture to obtain the title compound. MS (ESI) m/z 203.1 (M+H)+.

Workup

  1. customThe reaction mixture was evacuated
  2. customthen evacuated
  3. filtrationThe mixture was filtered through a celite pad
  4. concentrationthen concentrated
  5. customthe crude product was recrystallized in ethyl acetate/hexane mixture

Sources & evidence

ORD record
ord-82d3778ba2fd4d22800b97a118a72631
Source dataset
uspto-grants-2015_11
Patent number
US09181239B2

Reaction notes

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