HCID 18322365, compound → HCID 18322370, compound

HRID 1698897Notes

Reaction equation

HRID 1698897 reaction equation
[C:1]([C:11]1[S:12][C:13]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:14][C:15]=1[NH:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[O:18])([O:3]CC1C=CC=CC=1)=[O:2]>CCO.[Pd]>[C:1]([C:11]1[S:12][C:13]([C:27]([CH3:30])([CH3:29])[CH3:28])=[CH:14][C:15]=1[NH:16][C:17]([NH:19][C:20]1[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][CH:21]=1)=[O:18])([OH:3])=[O:2]

Participants

4

Reactant 1

HCID 18322365HCID 18322365, compound

Product 1

HCID 18322370HCID 18322370, compoundYield 90.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of N-(2-carbobenzyloxy-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.19 g, 0.40 mmol) in EtOH (19 mL) was added 10% Pd/C (0.010 g). The resulting suspension was treated with H2 (52 psi) in a Parr® shaker for 18 h. The slurry was filtered through a pad of Celite® and concentrated under reduced pressure to afford N-(2-carboxy-5-tert-butyl-3-thienyl)-N′-(4-methylphenyl)urea (0.12 g, 90%):1H NMR (d6-DMSO) δ13 (s, 9H), 2.2 (s, 3H), 7.1 (d, 2H), 7.4 (d, 2H), 7.8 (s, 1H); FAB-LRMS m/z) 333 (M+H).

Workup

  1. additionThe resulting suspension was treated with H2 (52 psi) in a Parr® shaker for 18 h
  2. filtrationThe slurry was filtered through a pad of Celite®
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-93c989ea650c4a34829ee4a12473b112
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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