3-(Trifluoromethyl)benzoic acid → HCID 46234711, compound

HRID 407156Notes

Reaction equation

HRID 407156 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:13][NH:14]3)=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.[F:22][C:23]([F:34])([F:33])[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27](O)=[O:28].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C>CN(C)C=O.O.C(OCC)(=O)C.C(N(CC)CC)C>[F:22][C:23]([F:33])([F:34])[C:24]1[CH:25]=[C:26]([CH:30]=[CH:31][CH:32]=1)[C:27]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:16]=[C:15]3[C:11]([C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[N:13][NH:14]3)=[CH:10][CH:9]=2)=[CH:6][CH:7]=1)=[O:28]

Participants

9

Reactant 4

HCID 99633-(Trifluoromethyl)benzoic acidHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 757711-HydroxybenzotriazoleHCID 53244426HCID 53244426, compound

Product 1

HCID 46234711HCID 46234711, compoundYield 72.3%

Reagents, catalysts & solvents 4

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

To a stirred solution of ethyl 6-(4-aminophenyl)-1H-indazole-3-carboxylate (40 mg), 3-trifluoromethyl-benzoic acid (35.2 mg), triethylamine (40 and HOBt (25 mg) in N,N-dimethylformamide, was added EDCI (40.6 mg). The mixture was stirred at 70° C. for 12 h. The mixture cooled to room temperature and ethyl acetate and water were added. The mixture was extracted with ethyl acetate three times. The combined organic layer was washed with saturated sodium bicarbonate solution, dried over sodium sulfate, and concentrated under reduced pressure. The residue was triturated by ethylacetate/hexane to give ethyl 6-(4-(3-(trifluoromethyl)benzamido)phenyl)-1H-indazole-3-carboxylate (46.6 mg).

Workup

  1. temperatureThe mixture cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate three times
  3. washThe combined organic layer was washed with saturated sodium bicarbonate solution
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was triturated by ethylacetate/hexane

Sources & evidence

ORD record
ord-1a1d1415a7e345a7a26c509af00ae18e
Source dataset
uspto-grants-2014_06
Patent number
US08754209B2

Reaction notes

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