Dichloromethane → HCID 59540941, compound

HRID 1677418Notes

Reaction equation

HRID 1677418 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][CH2:47][OH:48].[CH2:49]([Cl:51])[Cl:50]>CN(C)C=O.CO>[NH4+:7].[OH-:4].[Cl:50][CH2:49][Cl:51].[OH:48][CH2:47][CH2:46][N:23]1[CH2:24][CH2:25][N:20]([C:16]2[CH:15]=[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:19]=[CH:18][CH:17]=2)[CH2:21][CH2:22]1

Participants

8

Reactant 4

HCID 6344DichloromethaneHCID 108982-BromoethanolHCID 81531DiisopropylethylamineHCID 59540668HCID 59540668, compound

Product 2

HCID 21919329HCID 21919329, compoundHCID 59540941HCID 59540941, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 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 (0.10 g, 0.203 mmol) in 2 mL dimethyl formamide under argon was added 0.088 mL of diisopropylethylamine (0.066 g, 0.508 mmol) and 0.036 mL of 2-bromoethanol (0.0635 g, 0.508 mmol). The reaction was stirred overnight at room temperature 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 (0→40% 60:10:1 CH2Cl2:MeOH:NH4OH/dichloromethane over 30 minutes) afforded 0.0648 g (59% yield) of 1-[2-{3-[4-(2-Hydroxy-ethyl)-piperazin-1-yl]-phenyl}-5-(2-trimethylsilanyl-ethoxymethyl)-5H-pyrrolo[2,3-b]pyrazin-7-yl]-2,2-dimethyl-propan-1-one as a yellow oil. MS (E/I): 538 (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-52fcba92e366470587b03152f0a79ea0
Source dataset
uspto-grants-2011_08
Patent number
US08008298B2

Reaction notes

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