4-(Trifluoromethyl)phenyl isocyanate → HCID 58451262, compound

HRID 2366768Notes

Reaction equation

HRID 2366768 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([N:8]([CH3:24])[C:9]2[N:14]=[C:13]3[S:15][C:16]([NH:18][C:19]([CH:21]4[CH2:23][CH2:22]4)=[O:20])=[N:17][C:12]3=[CH:11][CH:10]=2)[CH:5]=[CH:6][CH:7]=1.[N:25]([C:28]1[CH:33]=[CH:32][C:31]([C:34]([F:37])([F:36])[F:35])=[CH:30][CH:29]=1)=[C:26]=[O:27].C(=O)([O-])O.[Na+]>CN(C)C=O>[CH3:24][N:8]([C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([NH:1][C:26](=[O:27])[NH:25][C:28]2[CH:33]=[CH:32][C:31]([C:34]([F:35])([F:37])[F:36])=[CH:30][CH:29]=2)[CH:3]=1)[C:9]1[N:14]=[C:13]2[S:15][C:16]([NH:18][C:19]([CH:21]3[CH2:22][CH2:23]3)=[O:20])=[N:17][C:12]2=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 737684-(Trifluoromethyl)phenyl isocyanateHCID 516892Sodium BicarbonateHCID 86657968HCID 86657968, compound

Product 1

HCID 58451262HCID 58451262, compoundYield 63.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of N-{5-[(3-aminophenyl)(methyl)amino][1,3]thiazolo[5,4-b]pyridin-2-yl}cyclopropanecarboxamide (100 mg, 0.295 mmol) produced in Example 8(x) in N,N-dimethylformamide (1.0 mL) was added 1-isocyanato-4-(trifluoromethyl)benzene (50.5 μL, 0.354 mmol), and the mixture was stirred at room temperature for 1 hr. Aqueous sodium hydrogen carbonate solution (20 mL) was added to the reaction mixture, and the mixture was extracted with ethyl acetate (50 mL). The organic layer was washed with saturated brine (20 mL), dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The precipitate was collected by filtration and recrystallized from hexane/tetrahydrofuran to give the title compound (98 mg, 63%) as a colorless powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (50 mL)
  2. washThe organic layer was washed with saturated brine (20 mL)
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. filtrationThe precipitate was collected by filtration
  6. customrecrystallized from hexane/tetrahydrofuran

Sources & evidence

ORD record
ord-fecd3d881a544189a1f56b33750d94b2
Source dataset
uspto-grants-2014_04
Patent number
US08697874B2

Reaction notes

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