HCID 25234656, compound → HCID 25234770, compound

HRID 1924458Notes

Reaction equation

HRID 1924458 reaction equation
[C:1]([C:5]1[C:6]([O:36][CH3:37])=[C:7]([CH:25]=[C:26]([N:28]2[CH:33]=[CH:32][C:31](=[O:34])[NH:30][C:29]2=[O:35])[CH:27]=1)/[CH:8]=[CH:9]/[C:10]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])([CH3:4])([CH3:3])[CH3:2]>CO.C1COCC1.[Pd]>[C:1]([C:5]1[C:6]([O:36][CH3:37])=[C:7]([CH:25]=[C:26]([N:28]2[CH:33]=[CH:32][C:31](=[O:34])[NH:30][C:29]2=[O:35])[CH:27]=1)[CH2:8][CH2:9][C:10]1[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[CH:16][C:11]=1[C:12]([O:14][CH3:15])=[O:13])([CH3:4])([CH3:2])[CH3:3]

Participants

5

Reactant 1

HCID 25234656HCID 25234656, compound

Product 1

HCID 25234770HCID 25234770, compoundYield 68.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of the product from Example 25 (40 mg, 0.076 mmol) in MeOH (2 ml) and THF (2 ml) was added 10% Pd/C (20 mg) and the resulting mixture was stirred at room temperature under 1 atm H2 for 16 h. The mixture was filtered through celite and concentrated in vacuo to give a solid (27.5 mg, 68%). 1H NMR (300 MHz, DMSO-d6) 11.39 (s, 1 H) 9.88 (s, 1 H) 7.61-7.71 (m, 2 H) 7.28-7.36 (m, 2 H) 7.20 (d, J=2.57 Hz, 1 H) 7.13 (d, J=2.94 Hz, 1 H) 5.64 (d, J=7.72 Hz, 1 H) 3.83 (s, 3 H) 3.75 (s, 3 H) 3.14 (dd, J=10.30, 5.88 Hz, 2 H) 2.96 (s, 3 H) 2.83-2.92 (m, 2 H) 1.34 (s, 9 H).

Workup

  1. filtrationThe mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7c79a28d8c4442e1b0fe9d94f64b9100
Source dataset
uspto-grants-2012_05
Patent number
US08178548B2

Reaction notes

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