HCID 16734504, compound → HCID 11238854, compound

HRID 2353581Notes

Reaction equation

HRID 2353581 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([N:18]2[C:22](=[O:23])[CH:21]=[C:20]([C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]([O:34][CH2:35][CH2:36][N:37]4[CH2:42][CH2:41][O:40][CH2:39][CH2:38]4)=[CH:26][CH:25]=3)[C:19]2=[O:43])[C:8]([O:16][CH3:17])=[C:9]([NH:11][S:12]([CH3:15])(=[O:14])=[O:13])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]>[Pd].C(O)C>[C:1]([C:5]1[CH:6]=[C:7]([N:18]2[C:22](=[O:23])[CH2:21][CH:20]([C:24]3[C:33]4[C:28](=[CH:29][CH:30]=[CH:31][CH:32]=4)[C:27]([O:34][CH2:35][CH2:36][N:37]4[CH2:38][CH2:39][O:40][CH2:41][CH2:42]4)=[CH:26][CH:25]=3)[C:19]2=[O:43])[C:8]([O:16][CH3:17])=[C:9]([NH:11][S:12]([CH3:15])(=[O:13])=[O:14])[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 16734504HCID 16734504, compound

Product 1

HCID 11238854HCID 11238854, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

In a 20 mL scintillation vial was placed (28 mg, 0.046 mmol) N-(5-tert-butyl-2-methoxy-3-{3-[4-(2-morpholin-4-yl-ethoxy)-naphthalen-1-yl]-2,5-dioxo-2,5-dihydro-pyrrol-1-yl}-phenyl)-methanesulfonamide, 5 mL ethanol, and Pd/C (15 mg, 10 mole%). The vial was sealed with a septum and the reaction mixture was sparged with house nitrogen for 10 minutes. The resulting solution was then sparged with hydrogen gas via a balloon for 5 minutes. After recharging the balloon with hydrogen gas the reaction was allowed to stir at room temp for 2 hours. The resulting solution was filtered through a pad of celite and concentrated under vacuum to afford the desired product (27 mg, 100%). Calculated mass=610. Observed mass=611.

Workup

  1. customThe vial was sealed with a septum
  2. customthe reaction mixture was sparged with house nitrogen for 10 minutes
  3. customThe resulting solution was then sparged with hydrogen gas via a balloon for 5 minutes
  4. filtrationThe resulting solution was filtered through a pad of celite
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-1db6c9c2ee7240b08a4a6a7093c1de33
Source dataset
uspto-grants-2010_07
Patent number
US07749999B2

Reaction notes

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