1-Chloro-4-isothiocyanato-2-(trifluoromethyl)benzene → HCID 42625162, compound

HRID 1864669Notes

Reaction equation

HRID 1864669 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[NH2:15][C:16]1[CH:32]=[CH:31][C:19]([O:20][C:21]2[CH:26]=[CH:25][N:24]=[C:23]3[NH:27][C:28](=[O:30])[NH:29][C:22]=23)=[CH:18][CH:17]=1>C1COCC1>[O:30]=[C:28]1[NH:27][C:23]2=[N:24][CH:25]=[CH:26][C:21]([O:20][C:19]3[CH:31]=[CH:32][C:16]([NH:15][C:9]([NH:8][C:5]4[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([C:11]([F:14])([F:12])[F:13])[CH:4]=4)=[S:10])=[CH:17][CH:18]=3)=[C:22]2[NH:29]1

Participants

4

Reactant 2

HCID 5200261-Chloro-4-isothiocyanato-2-(trifluoromethyl)benzeneHCID 426260467-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one

Product 1

HCID 42625162HCID 42625162, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-chloro-3-trifluoromethylphenyl-isothiocyanate (20 μL, 0.12 mmol) and 7-(4-aminophenoxy)-1H-imidazo[4,5-b]pyridin-2(3H)-one (29 mg, 0.12 mmol) in anhydrous THF (2 mL) was stirred at room temperature for 3 days. The solvent was evaporated and the solid residue was washed with DCM to afford the title compound (47 mg, 82%). 1H-NMR (δ, ppm, DMSO-d6): 6.40 (d, 1H, HPy,6, J=5.8 Hz), 7.15 (d, 2H, Harom,Ph,3+5, J=8.70 Hz), 7.54 (d, 2H, Harom,Ph,2+6, J=8.75 Hz), 7.67 (d, 1H, HPy,6, J=8.55 Hz), 7.80 (broad s, 2H, Harom′), 8.08 (s, 1H, Harom′), 10.03 (s, 1H, NHthiourea,1), 10.10 (s, 1H, NHthiourea,3), 11.18 (s, 1H, NHPy3), 11.36 (s, 1H, NHPy2).

Workup

  1. customThe solvent was evaporated
  2. washthe solid residue was washed with DCM

Sources & evidence

ORD record
ord-50aa7d571d2c402aa5b6603ab910dce8
Source dataset
uspto-grants-2009_12
Patent number
US07625922B2

Reaction notes

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