Chlorosuccinimide → HCID 67260717, compound

HRID 79266Notes

Reaction equation

HRID 79266 reaction equation
[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][CH:13]=[C:12]([NH2:17])[C:11]=2[C:10]([CH2:18][CH3:19])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Cl:20]N1C(=O)CCC1=O>C(#N)C>[CH2:1]([N:8]1[C:16]2[CH:15]=[CH:14][C:13]([Cl:20])=[C:12]([NH2:17])[C:11]=2[C:10]([CH2:18][CH3:19])=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 67259831HCID 67259831, compound

Product 1

HCID 67260717HCID 67260717, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
60 °C

Procedure

To a reaction vial was added 1-benzyl-3-ethyl-1H-indazol-4-amine (20.0 mg, 0.0796 mmol) (prepared as in Example 2, steps A-B), N-chlorosuccinimide (12.8 mg, 0.0955 mmol) and acetonitrile (0.4 mL). The reaction vial was sealed and heated, with magnetic stirring, at 60° C. for 4 hours. The mixture was stirred at ambient temperature for 16 hours. The solvent was removed under a stream of nitrogen. The resulting material was purified using preparative thin layer chromatography on silica, eluting with 5% methanol in chloroform containing 0.5% ammonium chloride solution. The desired mono-chlorination product, 1-benzyl-5-chloro-3-ethyl-1H-indazol-4-amine (MS, APCI, m/z=286.1, M+H) was isolated as lower eluting component (8.7 mg).

Workup

  1. customThe reaction
  2. customvial was sealed
  3. customThe solvent was removed under a stream of nitrogen
  4. customThe resulting material was purified
  5. washeluting with 5% methanol in chloroform containing 0.5% ammonium chloride solution

Sources & evidence

ORD record
ord-687992e5eebd44ce9db023f9dadfeef7
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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