Chloroacetyl chloride → HCID 86700406, compound

HRID 879593Notes

Reaction equation

HRID 879593 reaction equation
[NH2:1][CH2:2][CH:3]([C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)[OH:4].[Cl:15][CH2:16][C:17](Cl)=[O:18].CCN(C(C)C)C(C)C>CN(C=O)C>[Cl:15][CH2:16][C:17]([NH:1][CH2:2][CH:3]([OH:4])[C:5]1[CH:13]=[C:12]2[C:8]([CH:9]=[N:10][N:11]2[CH3:14])=[CH:7][CH:6]=1)=[O:18]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 86700407HCID 86700407, compound

Product 1

HCID 86700406HCID 86700406, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To the crude material 2-amino-1-(1-methyl-1H-indazol-6-yl)ethanol (390.8 mg, ˜50%, ˜1 mmol)in DMF was then added 2-chloroacetyl chloride (138.7 mg, 1.2 mmol) and iPr2NEt (0.347 mL, 2 mmol). The resulting mixture was stirred at room temperature for 2 hr. The mixture was then taken into partition between EtOAc and brine. The organic layer was separated and the aqueous layer was extracted with EtOAc twice. The combined organic layers were dried dried (Na2SO4), filtered and evaporated to dryness. The residue was purified on CombiFlash (50% EtOAc/Hex) to give 2-chloro-N-(2-hydroxy-2-(1-methyl-1H-indazol-6-yl)ethyl)acetamide. LCMS-ESI+: calc'd for C12H14ClN3O2: 268.1, 270.1 (M+H+); found: 268.2, 270.2 (M+H+).

Workup

  1. custominto partition between EtOAc and brine
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc twice
  4. customThe combined organic layers were dried
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThe residue was purified on CombiFlash (50% EtOAc/Hex)

Sources & evidence

ORD record
ord-7fb367c79d57473c9fedaef478d07708
Source dataset
uspto-grants-2015_03
Patent number
US08987250B2

Reaction notes

Loading…