tert-Butyl bromoacetate → HCID 59540602, compound

HRID 1677419Notes

Reaction equation

HRID 1677419 reaction equation
[CH3:1][C:2]([CH3:35])([CH3:34])[C:3]([C:5]1[C:13]2[C:8](=[N:9][CH:10]=[C:11]([C:14]3[CH:19]=[CH:18][CH:17]=[C:16]([N:20]4[CH2:25][CH2:24][NH:23][CH2:22][CH2:21]4)[CH:15]=3)[N:12]=2)[N:7]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[CH:6]=1)=[O:4].C(N(C(C)C)CC)(C)C.Br[CH2:46][C:47]([O:49][C:50]([CH3:53])([CH3:52])[CH3:51])=[O:48]>CN(C)C=O>[C:50]([O:49][C:47](=[O:48])[CH2:46][N:23]1[CH2:24][CH2:25][N:20]([C:16]2[CH:17]=[CH:18][CH:19]=[C:14]([C:11]3[N:12]=[C:13]4[C:5]([C:3](=[O:4])[C:2]([CH3:35])([CH3:34])[CH3:1])=[CH:6][N:7]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:31])([CH3:33])[CH3:32])[C:8]4=[N:9][CH:10]=3)[CH:15]=2)[CH2:21][CH2:22]1)([CH3:53])([CH3:52])[CH3:51]

Participants

5

Reactant 3

HCID 79177tert-Butyl bromoacetateHCID 81531DiisopropylethylamineHCID 59540668HCID 59540668, compound

Product 1

HCID 59540602HCID 59540602, compoundYield 61.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2,2-Dimethyl-1-[2-(3-piperazin-1-yl-phenyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-propan-1-one (0.233 g, 0.473 mmol) in 2 mL of dimethyl formamide was added 0.074 mL of diisopropylethylamine (0.055 g, 0.425 mmol) and 0.629 mL of tert-butyl bromoacetate (0.083 g, 0.425 mmol). The reaction was stirred at room temperature overnight before quenching with water and extracting with dichloromethane. The combined organics were washed with water, dried over MgSO4, filtered and concentrated in vacuo. Silica gel chromatography (10→60% EtOAc/hexanes over 30 minutes) afforded 0.1582 g (61% yield) of (4-{3-[7-(2,2-Dimethyl-propionyl)-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-2-yl]-phenyl}-piperazin-1-yl)-acetic acid tert-butyl ester as a yellow oil. MS (E/I): 608 (M+H).

Workup

  1. custombefore quenching with water
  2. extractionextracting with dichloromethane
  3. washThe combined organics were washed with water
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-7045faa10a7d4fc1aec57c8e090e233c
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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