Sulfuric Acid → HCID 67976421, compound

HRID 706685Notes

Reaction equation

HRID 706685 reaction equation
[F:1][C:2]([F:21])([F:20])[C:3]1[CH:4]=[C:5]([CH:17]=[CH:18][CH:19]=1)[CH2:6][N:7]1[C:15]2[CH:14]=[CH:13][CH:12]=[C:11]([NH2:16])[C:10]=2[CH:9]=[N:8]1.OS(O)(=O)=O.[Cl:27]N1C(=O)CCC1=O.C(=O)([O-])[O-].[Na+].[Na+]>C1COCC1.O>[Cl:27][C:12]1[CH:13]=[CH:14][C:15]2[N:7]([CH2:6][C:5]3[CH:17]=[CH:18][CH:19]=[C:3]([C:2]([F:1])([F:20])[F:21])[CH:4]=3)[N:8]=[CH:9][C:10]=2[C:11]=1[NH2:16]

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 31398ChlorosuccinimideHCID 679763551-(3-(trifluoromethyl)benzyl)-1H-indazol-4-amine

Product 1

HCID 67976421HCID 67976421, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1-(3-(trifluoromethyl)benzyl)-1H-indazol-4-amine (0.056 g, 0.192 mmol) in THF (1.0 mL) was cooled to −78° C. under N2. H2SO4 (0.00512 mL, 0.0961 mmol) was added and the mixture was stirred for 5 minutes. N-chlorosuccinimide (0.0257 g, 0.192 mmol) was added in one portion and the reaction was stirred at −78° C. for 1 hour. Sodium carbonate (0.0204 g, 0.192 mmol) was added and the mixture was warmed to ambient temperature. The mixture was diluted with water (5 mL) and extracted with EtOAc (3×10 mL). The combined organic layers were then washed with brine and dried over Na2SO4, filtered and concentrated. The crude product was purified by preparative TLC (40% EtOAc/hexane) in which two major bands were observed. The higher band was determined to be the title compound (0.028 g, 44%) and was isolated as a dark yellow/green solid.

Workup

  1. stirringthe reaction was stirred at −78° C. for 1 hour
  2. extractionextracted with EtOAc (3×10 mL)
  3. washThe combined organic layers were then washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified by preparative TLC (40% EtOAc/hexane) in which two major bands
  8. customwas isolated as a dark yellow/green solid

Sources & evidence

ORD record
ord-3afc3dbc1e994d3ab9c7ceda564b9249
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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