3-(Trifluoromethyl)phenyl isocyanate → HCID 121276431, compound

HRID 2205566Notes

Reaction equation

HRID 2205566 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([P:8](=[O:13])([O:11][CH3:12])[O:9][CH3:10])=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([NH2:20])=[CH:16][CH:15]=1.[N:21]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=1)=[C:22]=[O:23]>CN(C=O)C.C(OCC)(=O)C>[NH2:1][C:2]1[N:7]=[CH:6][C:5]([P:8](=[O:13])([O:11][CH3:12])[O:9][CH3:10])=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:22]([NH:21][C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:31])([F:32])[F:33])[CH:25]=2)=[O:23])=[CH:16][CH:15]=1

Participants

5

Reactant 2

HCID 94833-(Trifluoromethyl)phenyl isocyanateHCID 125501477HCID 125501477, compound

Product 1

HCID 121276431HCID 121276431, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

The reaction mixture of dimethyl (6-amino-5-(4-aminophenyl)pyridin-3-yl)phosphonate (30 mg, 0.10 mmol, 1 eq) and 1-isocyanato-3-(trifluoromethyl)benzene (0.018 mL, 1.2 eq) in anhydrous DMF (0.5 mL) under anhydrous nitrogen atmosphere was stirred at room temperature for an hour. It was then diluted with ethyl acetate, washed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine, and lastly dried with anhydrous sodium sulfate. The upper clear solution was decanted, concentrated, and the solid residue was subject to a gradient column chromatography (EtOAc-Hex 2:1 to MeOH-EtOAc 1:20) to yield dimethyl (6-amino-5-(4-(3-(3-(trifluoromethyl)phenyl)ureido)phenyl)pyridin-3-yl)phosphonate as a white solid in amount of 41 mg.

Workup

  1. washwashed sequentially with aqueous ammonium chloride, saturated aqueous sodium bicarbonate, brine
  2. dry with materiallastly dried with anhydrous sodium sulfate
  3. customThe upper clear solution was decanted
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-891023cb3ab344579d28b136afbd888b
Source dataset
uspto-grants-2016_06
Patent number
US09371314B2

Reaction notes

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