HCID 178490697, compound → HCID 178490696, compound

HRID 76252Notes

Reaction equation

HRID 76252 reaction equation
[N:1]([CH2:4][CH2:5][C:6]1=[CH:7][N:8]([C:23]([CH3:26])([CH3:25])[CH3:24])[S:9]/[C:10]/1=[N:11]\[C:12](=[O:22])[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[O:20][CH3:21])=[N+]=[N-]>CCO.[Pd]>[NH2:1][CH2:4][CH2:5][C:6]1=[CH:7][N:8]([C:23]([CH3:26])([CH3:25])[CH3:24])[S:9]/[C:10]/1=[N:11]\[C:12](=[O:22])[C:13]1[CH:18]=[C:17]([Cl:19])[CH:16]=[CH:15][C:14]=1[O:20][CH3:21]

Participants

4

Reactant 1

HCID 178490697HCID 178490697, compound

Product 1

HCID 178490696HCID 178490696, compoundYield 91%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

The product from Example 14 (70 mg, 0.18 mmol) in EtOH (10 mL) was treated with Pd/C (10 mg) under a hydrogen balloon for 3 hrs. The Pd/C was filtered off and washed with EtOH. The filtrate was concentrated to afford 60 mg (91%) of the title compound. 1H NMR (500 MHz, CDCl3) δ ppm 1.68 (s, 9 H) 3.08 (dd, J=5.80, 4.88 Hz, 2 H) 3.27 (dd, J=5.19 Hz, 2 H) 3.92 (s, 3 H) 6.94 (d, J=8.85 Hz, 1 H) 7.37 (dd, J=8.85, 2.75 Hz, 1 H) 7.97 (d, J=2.75 Hz, 1 H) 8.03 (s, 1 H); MS (DCI/NH4+) m/z 368 (M+H)+.

Workup

  1. filtrationThe Pd/C was filtered off
  2. washwashed with EtOH
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-dcb8e5557f644e3c9deb20c3296e3a1e
Source dataset
uspto-grants-2014_09
Patent number
US08835475B2

Reaction notes

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