Carbonate Ion → HCID 59265101, compound

HRID 646296Notes

Reaction equation

HRID 646296 reaction equation
N=C=N.[CH3:4][O:5][C:6]1[C:11]([C:12]([OH:14])=O)=[CH:10][C:9]([C:15]([NH2:17])=[O:16])=[CH:8][CH:7]=1.O.N1(O)C2C=CC=CC=2N=N1.[Br:29][C:30]1[CH:36]=[CH:35][C:33]([NH2:34])=[C:32]([F:37])[CH:31]=1.C([NH+](CC)CC)C.C(=O)([O-])[O-]>CN(C)C=O>[Br:29][C:30]1[CH:36]=[CH:35][C:33]([NH:34][C:12](=[O:14])[C:11]2[CH:10]=[C:9]([CH:8]=[CH:7][C:6]=2[O:5][CH3:4])[C:15]([NH2:17])=[O:16])=[C:32]([F:37])[CH:31]=1

Participants

8

Reactant 6

HCID 19660Carbonate IonHCID 1230504-Bromo-2-fluoroanilineHCID 160435CarbodiimideHCID 1385867TriethylammoniumHCID 27960291-Hydroxybenzotriazole hydrateHCID 132228085-Carbamoyl-2-methoxybenzoic acid

Product 1

HCID 59265101HCID 59265101, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

To 202 mg (1.24 mmols/g) of N-cyclohexylcarbodiimide-N′-propyloxymethylpolystyrene (PS-carbodiimide), there were added 0.5 mL (0.25 mol) of an N,N-dimethylformamide solution of 6-methoxyisophthalamic acid prepared in step B, 0.75 mL (0.25M) of an N,N-dimethylformamide solution of benzotriazol-1-ol monohydrate, and 20 mg of 4-bromo-2-fluoroaniline. This mixture was agitated for 16 hours at room temperature, and then agitated for 24 hours at 60° C. To the mixture, 213 mg (2.64 mmols/g) of macroporous triethylammonium methylpolystyrene carbonate (MP-carbonate) and 0.5 mL of N,N-dimethylformamide were added, followed by agitating the mixture for 12 hours at room temperature. The polystyrene solid phase-carried reagent was separated by filtration, and washed with N,N-dimethylformamide, tetrahydrofuran, and dichloromethane in this order. Then, the filtrate and the washings were combined, and concentrated. The resulting residue was purified using a micromass spectrometer (ZMD produced by Micromass) equipped with a gradient high-performance liquid chromatograph 996-600E produced by Waters, thereby obtaining 9 mg (22%) of 3-N-(4-bromo-2-fluorophenyl)-4-methoxyisophthalamide.

Workup

  1. stirringagitated for 24 hours at 60° C
  2. stirringby agitating the mixture for 12 hours at room temperature
  3. customThe polystyrene solid phase-carried reagent was separated by filtration
  4. washwashed with N,N-dimethylformamide, tetrahydrofuran, and dichloromethane in this order
  5. concentrationconcentrated
  6. customThe resulting residue was purified
  7. customa micromass spectrometer (ZMD produced by Micromass)
  8. customequipped with a gradient high-performance liquid chromatograph 996-600E
  9. customproduced by Waters

Sources & evidence

ORD record
ord-8d9da5cccd5240d8934b7b38da35b54d
Source dataset
uspto-grants-2010_04
Patent number
US07705053B2

Reaction notes

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