N-bromobutanimide → HCID 58382313, compound

HRID 1628124Notes

Reaction equation

HRID 1628124 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:13]=[CH:12][N:11]([Si](C(C)C)(C(C)C)C(C)C)[C:8]=3[N:9]=[CH:10][C:5]2=[C:4]([C:24]2[CH:29]=[CH:28][C:27]([C:30]([OH:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=2)[N:3]=1.C1C(=O)N([Br:41])C(=O)C1>C(Cl)Cl>[Br:41][C:12]1[NH:11][C:8]2[N:9]=[CH:10][C:5]3[N:6]([C:2]([CH3:1])=[N:3][C:4]=3[C:24]3[CH:29]=[CH:28][C:27]([C:30]([OH:33])([CH3:32])[CH3:31])=[CH:26][CH:25]=3)[C:7]=2[CH:13]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 58382017HCID 58382017, compound

Product 1

HCID 58382313HCID 58382313, compoundYield 18%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 2-(4-(1-methyl-6-(triisopropylsilyl)-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (0.755 g, 1.63 mmol, Preparation #AX.1) in DCM (16.3 ml) at about −20° C. was added NBS (0.462 g, 2.59 mmol). The resulting suspension was allowed to stir at about −20° C. for about 15 min. The mixture was concentrated under reduced pressure and the residue was purified by flash chromatography (40 g silica gel column; gradient elution with 0 to 50% EtOAc/heptane) to give 2-(4-(7-bromo-1-methyl-6H-imidazo[1,5-a]pyrrolo[2,3-e]pyrazin-3-yl)phenyl)propan-2-ol (0.11 g, 18%). LC/MS (Table 2, Method a) Rt=2.41 min; MS m/z 385 (M+H)+. Syk IC50=B.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash chromatography (40 g silica gel column; gradient elution with 0 to 50% EtOAc/heptane)

Sources & evidence

ORD record
ord-9ff5abccea5447b381bfe198c9b6822e
Source dataset
uspto-grants-2014_07
Patent number
US08785639B2

Reaction notes

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