Water → HCID 22174484, compound

HRID 1797320Notes

Reaction equation

HRID 1797320 reaction equation
[CH3:1][C:2](=[CH2:11])[C:3]([O:5][CH2:6][CH2:7][N:8]=[C:9]=[O:10])=[O:4].[NH2:12][C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[O:28])=[C:23]([Cl:36])[CH:22]=1.O.CCOC(C)=O>N1C=CC=CC=1>[CH3:11][C:2](=[CH2:1])[C:3]([O:5][CH2:6][CH2:7][NH:8][C:9]([NH:12][C:13]1[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=1[NH:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:28])[C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])=[C:23]([Cl:36])[CH:22]=1)=[O:10])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 354092-Isocyanatoethyl methacrylateHCID 9801969EO-1428

Product 1

HCID 22174484HCID 22174484, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

2-Isocyanatoethyl 2-methylacrylate (0.31 g, 2.2 mmol) was slowly added to a solution of {4-[(2-amino-4-bromophenyl)amino]-2-chlorophenyl}(2-methylphenyl)methanone (0.60 g, 1.44 mmol)(disclosed in WO 01/05744) in dry pyridine (3.00 mL). The solution was stirred at room temperature for 6 h after which it was poured into a mixture of water and EtOAc. The aqueous phase was extracted with more EtOAc (×2). The combined organic phases were washed with brine, dried (MgSO4), filtered and concentrated in vacuo. The crude product was purified by flash chromatography using petroleum ether/EtOAc 4:1 as the eluent to afford the title compound as a light brown solid.

Workup

  1. extractionThe aqueous phase was extracted with more EtOAc (×2)
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-53a287d3734242fc864f469153df2d91
Source dataset
uspto-grants-2006_04
Patent number
US07034015B2

Reaction notes

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