HCID 2756400, compound → HCID 24960192, compound

HRID 244405Notes

Reaction equation

HRID 244405 reaction equation
Cl.[F:2][C:3]([F:23])([F:22])[CH:4]([NH2:21])[C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[N:9]=[CH:8]2.[NH2:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[C:26]=1[S:33](Cl)(=[O:35])=[O:34]>N1C=CC=CC=1.Cl>[NH2:24][C:25]1[CH:30]=[C:29]([Cl:31])[CH:28]=[C:27]([Cl:32])[C:26]=1[S:33]([NH:21][CH:4]([C:5]1[CH:6]=[C:7]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:14]1[CH:15]=[CH:16][C:17]([F:20])=[CH:18][CH:19]=1)[N:9]=[CH:8]2)[C:3]([F:2])([F:22])[F:23])(=[O:35])=[O:34]

Participants

5

Reactant 2

HCID 2756400HCID 2756400, compoundHCID 68475013HCID 68475013, compound

Product 1

HCID 24960192HCID 24960192, compoundYield 19.7%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 1049PyridineSolvent

Procedure

A mixture of 60 mg (0.19 mmol) of 2,2,2-trifluoro-1-[1-(4-fluorophenyl)-1H-indazol-5-yl]ethylamine hydrochloride and 51 mg (0.19 mmol) of 2-amino-4,6-dichlorobenzenesulfonyl chloride in 8 mL of pyridine was stirred at room temperature for 1 hour and then warmed at 65° C. for 4 hours. The mixture was cooled to room temperature and diluted with 1N aqueous HCl and extracted with ethyl acetate. The combined organic layers were washed with saturated sodium bicarbonate, brine, dried over sodium sulfate, decanted, and concentrated in vacuo. The crude material was first purified by Combiflash chromatography using EtOAc-hexanes (0-60% gradient) and then by preparative TLC using EtOAc-hexanes (2:8) to provide 20 mg (17%) of the title compound as a colorless foam. MS m/z 534 (MH+).

Workup

  1. temperaturewarmed at 65° C. for 4 hours
  2. temperatureThe mixture was cooled to room temperature
  3. extractionextracted with ethyl acetate
  4. washThe combined organic layers were washed with saturated sodium bicarbonate, brine
  5. dry with materialdried over sodium sulfate
  6. customdecanted
  7. concentrationconcentrated in vacuo
  8. customThe crude material was first purified by Combiflash chromatography

Sources & evidence

ORD record
ord-da2bf290de2640ef84e503deba602bd7
Source dataset
uspto-grants-2014_02
Patent number
US08658637B2

Reaction notes

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