p-(Trifluoromethoxy)phenyl isocyanate → HCID 22502354, compound

HRID 1814715Notes

Reaction equation

HRID 1814715 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][CH:12]([C:14]2[CH:27]=[CH:26][C:17]([C:18]([NH:20][C:21]3[N:22]=[N:23][NH:24][N:25]=3)=[O:19])=[CH:16][CH:15]=2)[CH3:13])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[F:28][C:29]([F:41])([F:40])[O:30][C:31]1[CH:36]=[CH:35][C:34]([N:37]=[C:38]=[O:39])=[CH:33][CH:32]=1>CN(C=O)C>[C:1]([C:5]1[CH:6]=[CH:7][C:8]([N:11]([CH:12]([C:14]2[CH:27]=[CH:26][C:17]([C:18]([NH:20][C:21]3[N:22]=[N:23][NH:24][N:25]=3)=[O:19])=[CH:16][CH:15]=2)[CH3:13])[C:38]([NH:37][C:34]2[CH:35]=[CH:36][C:31]([O:30][C:29]([F:28])([F:40])[F:41])=[CH:32][CH:33]=2)=[O:39])=[CH:9][CH:10]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 92298p-(Trifluoromethoxy)phenyl isocyanateHCID 22501827HCID 22501827, compound

Product 1

HCID 22502354HCID 22502354, compoundYield 8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

4-[1-(4-tert-Butylphenylamino)ethyl]-N-(2H-tetrazol-5-yl)benzamide (100 mg, 0.28 mmol) and 4-trifluoromethoxyphenyl isocyanate (70 mg, 0.30 mmol) was dissolved in DMF (0.6 mL) and the solution was heated to 80° C. for 3 hours. The mixture was cooled to room temperature and subsequently taken to dryness using rotary evaporation. The residual oil was dissolved in a minimum of DMF/acetonitrile (1:1), and submitted to preparative HPLC purification. Pure fractions were pooled and concentrated to dryness to afford 10 mg (8%) of the title compound.

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customevaporation
  3. dissolutionThe residual oil was dissolved in a minimum of DMF/acetonitrile (1:1)
  4. customHPLC purification
  5. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-69469730bf94400da4a7948d3037dc21
Source dataset
uspto-grants-2005_04
Patent number
US06875760B2

Reaction notes

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