Chlorosuccinimide → HCID 86665175, compound

HRID 1893722Notes

Reaction equation

HRID 1893722 reaction equation
C1C(=O)N([Cl:8])C(=O)C1.[CH3:9][O:10][C:11]1[CH:28]=[CH:27][C:14]([CH2:15][N:16]2[CH:20]=[C:19]([C:21]3[N:22]=[C:23]([NH2:26])[S:24][CH:25]=3)[CH:18]=[N:17]2)=[CH:13][CH:12]=1>C(#N)C>[CH3:9][O:10][C:11]1[CH:12]=[CH:13][C:14]([CH2:15][N:16]2[CH:20]=[C:19]([C:21]3[N:22]=[C:23]([NH2:26])[S:24][C:25]=3[Cl:8])[CH:18]=[N:17]2)=[CH:27][CH:28]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86665174HCID 86665174, compound

Product 1

HCID 86665175HCID 86665175, compoundYield 29%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

According to Scheme 6, Step 2: NCS (8.14 mmol, 1.09 g) was added to a solution of 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)thiazol-2-amine (8.14 mmol, 2.33 g) in acetonitrile (20 mL) and the reaction mixture was stirred under reflux for 1.5 hour. After evaporation of the solvent, the crude residue was diluted in EtOAc. The organic phase was washed with water and brine, was dried over Na2SO4, was filtered and was concentrated. The crude mixture was purified by flash chromatography over silica gel using DCM/MeOH (100:0 to 90:10) as eluent to yield 4-(1-(4-methoxybenzyl)-1H-pyrazol-4-yl)-5-chlorothiazol-2-amine (2.35 mmol, 755 mg, 29%).

Workup

  1. temperatureunder reflux for 1.5 hour
  2. customAfter evaporation of the solvent
  3. additionthe crude residue was diluted in EtOAc
  4. washThe organic phase was washed with water and brine
  5. dry with materialwas dried over Na2SO4
  6. filtrationwas filtered
  7. concentrationwas concentrated
  8. customThe crude mixture was purified by flash chromatography over silica gel

Sources & evidence

ORD record
ord-eb86bf52aca1476b994754b7d8d328eb
Source dataset
uspto-grants-2013_08
Patent number
US08513252B2

Reaction notes

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