Acetyl chloride → HCID 58382178, compound

HRID 1628126Notes

Reaction equation

HRID 1628126 reaction equation
[C:1](Cl)(C)=O.[CH3:5][C:6]1[N:10]2[C:11]3[CH:17]=[CH:16][NH:15][C:12]=3[N:13]=[CH:14][C:9]2=[C:8]([C:18]2[CH:19]=[N:20][N:21]([CH2:23][C:24]([OH:26])=[O:25])[CH:22]=2)[N:7]=1>CO>[CH3:5][C:6]1[N:10]2[C:11]3[CH:17]=[CH:16][NH:15][C:12]=3[N:13]=[CH:14][C:9]2=[C:8]([C:18]2[CH:19]=[N:20][N:21]([CH2:23][C:24]([O:26][CH3:1])=[O:25])[CH:22]=2)[N:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 53247622HCID 53247622, compound

Product 1

HCID 58382178HCID 58382178, compoundYield 40%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

AcCl (20 mL) was added slowly with stirring to MeOH (100 mL) that was cooled in an ice bath. After about 1 h the solution was transferred to the 2-(4-(1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)-1H-pyrazol-1-yl)acetic acid. The solvents were removed under reduced pressure and saturated Na2CO3 (25 mL) was added. The product was extracted with DCM (5×20 mL). The combined organic layers were dried over MgSO4, filtered, and concentrated in vacuo. The residue was purified by flash chromatography (40 g silica gel) and eluted with a gradient of 2-9% MeOH in DCM to give methyl 2-(4-(1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)-1H-pyrazol-1-yl)acetate (0.109 g, 40%): LCMS (Table 2, Method b) Rt=1.46 min.; MS m/z: 311 (M+H)+. Syk IC50=B.

Workup

  1. temperaturewas cooled in an ice bath
  2. customThe solvents were removed under reduced pressure and saturated Na2CO3 (25 mL)
  3. additionwas added
  4. extractionThe product was extracted with DCM (5×20 mL)
  5. dry with materialThe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash chromatography (40 g silica gel)
  9. washeluted with a gradient of 2-9% MeOH in DCM

Sources & evidence

ORD record
ord-2652cef1329843debbdc4168fac7009f
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

Loading…