3,4-Dichlorophenyl isocyanate → HCID 68527229, compound

HRID 1932520Notes

Reaction equation

HRID 1932520 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][CH2:16][C:17]([N:19]3[CH2:24][CH2:23][N:22]([CH2:25][C:26]4[CH:34]=[CH:33][C:32]5[O:31][CH2:30][O:29][C:28]=5[CH:27]=4)[CH2:21][CH2:20]3)=[O:18])=[CH:11][CH:10]=2)=[N:6][CH:7]=1.C(N(C(C)C)C(C)C)C.[Cl:44][C:45]1[CH:46]=[C:47]([N:52]=[C:53]=[O:54])[CH:48]=[CH:49][C:50]=1[Cl:51]>C1(C)C=CC=CC=1>[CH2:25]([N:22]1[CH2:23][CH2:24][N:19]([C:17](=[O:18])[CH2:16][CH2:15][C:12]2[CH:11]=[CH:10][C:9]([O:8][C:5]3[N:6]=[CH:7][C:2]([NH:1][C:53]([NH:52][C:47]4[CH:48]=[CH:49][C:50]([Cl:51])=[C:45]([Cl:44])[CH:46]=4)=[O:54])=[CH:3][CH:4]=3)=[CH:14][CH:13]=2)[CH2:20][CH2:21]1)[C:26]1[CH:34]=[CH:33][C:32]2[O:31][CH2:30][O:29][C:28]=2[CH:27]=1

Participants

5

Reactant 3

HCID 76073,4-Dichlorophenyl isocyanateHCID 81531DiisopropylethylamineHCID 68524377HCID 68524377, compound

Product 1

HCID 68527229HCID 68527229, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a solution of 3-[4-(5-aminopyridin-2-yloxy)phenyl]-1-(4-piperonylpiperazin-1-yl)propane-1-one (600 mg, 1.3 mmol) in toluene (20 mL) were added ethyldiisopropylamine (0.454 mL, 2.6 mmol) and 3,4-dichlorophenylisocyanate (270 mg, 1.4 mmol), and the resulting solution was stirred for 1 day under reflux. The reaction solution was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (methanol:chloroform=1:19), and then recrystallized from ethyl acetate to thereby yield 280 mg of the title compound.

Workup

  1. temperatureunder reflux
  2. customThe reaction solution was evaporated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (methanol:chloroform=1:19)
  4. customrecrystallized from ethyl acetate to thereby yield 280 mg of the title compound

Sources & evidence

ORD record
ord-4eb12113ce5845efabfc8697ee00c62d
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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