HCID 59427845, compound → HCID 59427886, compound

HRID 502734Notes

Reaction equation

HRID 502734 reaction equation
[O:1]1[CH2:6][CH2:5][N:4]([CH2:7][CH2:8][NH:9][C:10]([NH:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-])=O)=[CH:15][C:14]=2[C:22]([F:25])([F:24])[F:23])=[O:11])[CH2:3][CH2:2]1>CCOC(C)=O.CO.[Pd]>[NH2:19][C:16]1[CH:17]=[CH:18][C:13]([NH:12][C:10]([NH:9][CH2:8][CH2:7][N:4]2[CH2:3][CH2:2][O:1][CH2:6][CH2:5]2)=[O:11])=[C:14]([C:22]([F:25])([F:24])[F:23])[CH:15]=1

Participants

5

Reactant 1

HCID 59427845HCID 59427845, compound

Product 1

HCID 59427886HCID 59427886, compound

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 1-(2-morpholinoethyl)-3-(4-nitro-2-(trifluoromethyl)phenyl)urea (651 mg, 1.80 mmol, 1.0 equiv) and 10% Pd/C (20 mg) in EtOAc (25 mL) and MeOH (2 mL) was exposed to an atmosphere of H2 (balloon). Upon completion of the reduction, the reaction mixture was filtered through celite and concentrated in vacuo to afford 1-(4-amino-2-(trifluoromethyl)phenyl)-3-(2-morpholinoethyl)urea, which was advanced without further purification. MS m/z: 333 (M+H+); Calculated for C14H19F3N4O2: 332.2

Workup

  1. filtrationUpon completion of the reduction, the reaction mixture was filtered through celite and
  2. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d26144d9739b43bdb611e627569e13c1
Source dataset
uspto-grants-2010_08
Patent number
US07776869B2

Reaction notes

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