HCID 18322372, compound → HCID 9946237, compound

HRID 1698887Notes

Reaction equation

HRID 1698887 reaction equation
[C:1]([C:5]1[S:6][C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:8][C:9]=1[NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[N+:20]([O-])=O)=[O:12])([O:3][CH3:4])=[O:2]>CO.[Pd]>[C:1]([C:5]1[S:6][C:7]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:8][C:9]=1[NH:10][C:11]([NH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[NH2:20])=[O:12])([O:3][CH3:4])=[O:2]

Participants

4

Reactant 1

HCID 18322372HCID 18322372, compound

Product 1

HCID 9946237HCID 9946237, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A slurry of N-(2-carbomethoxy-5-tert-butyl-3-thienyl)-N′-(2-nitrophenyl)urea (0.078 g, 0.21 mmol) and 10% Pd/C (0.010 g) in MeOH (15 mL) was stirred under H2 (1 atm.) for 18 h at 20° C. Celite® was added and the slurry was filtered. The resulting solution was concentrated under reduced pressure and the residue was purified by flash chromatography (gradient from 20% EtOAc/hexane to 50% EtOAc/hexane) to afford N-(2-carbomethoxy-5-tert-butyl-3-thienyl)-N′-(2-aminophenyl)urea as a foam (0.060 g, 83%): 1H NMR (CDCl3, partial spectrum) δ1.4 (s, 9H), 3.6 (s, 3H), 6.8-7.3 (m, 4H), 7.8 (s, 1H), 9.6 (s, 1H); FAB-LRMS m/z (rel abundance) 348 (M+H, 34%).

Workup

  1. additionCelite® was added
  2. filtrationthe slurry was filtered
  3. concentrationThe resulting solution was concentrated under reduced pressure
  4. customthe residue was purified by flash chromatography (gradient from 20% EtOAc/hexane to 50% EtOAc/hexane)

Sources & evidence

ORD record
ord-d5fafa3be13846f1ab0817528b28c6f1
Source dataset
uspto-grants-2002_02
Patent number
US06344476B1

Reaction notes

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