HCID 59427845, compound → HCID 59427886, compound

HRID 1042689Notes

Reaction equation

HRID 1042689 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-6694a3a71f924be797b5c21585674e23
Source dataset
uspto-grants-2013_10
Patent number
US08557996B2

Reaction notes

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