Cesium carbonate → HCID 57556618, compound

HRID 1777727Notes

Reaction equation

HRID 1777727 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[N:9][C:4]=2[NH:3][CH:2]=1.Br[CH2:11][C:12]([O:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13].C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C.CC(=O)OCC>[CH2:15]([O:14][C:12](=[O:13])[CH2:11][N:3]1[C:4]2=[N:9][CH:8]=[CH:7][CH:6]=[C:5]2[N:1]=[CH:2]1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 62576Benzyl bromoacetateHCID 178420746HCID 178420746, compound

Product 1

HCID 57556618HCID 57556618, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a brown solution of 4-azabenzimidazole (4.75 g) in DMF (80 mL) was added benzyl bromoacetate (6.58 mL) followed by Cs2CO3 (25.9 g). The resulting light brown suspension was stirred overnight. The reaction mixture was diluted with EA and washed twice with water and aq. sat. NH4Cl. The aq. layers were extracted twice with EA. The combined org. layers were dried over MgSO4, filtrated off and evaporated in reduced pressure. The crude was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8:2; gradient in % B: 0 to 5 over 3CV, 5 for 5CV, 5 to 15 over 5CV, 15% B for 3CV) to afford 4.99 g of the desired compound as yellow solid. LC-MS (C): tR=0.59 min; [M+H]+: 267.86.

Workup

  1. washwashed twice with water and aq. sat. NH4Cl
  2. extractionThe aq. layers were extracted twice with EA
  3. dry with materiallayers were dried over MgSO4
  4. filtrationfiltrated off
  5. customevaporated in reduced pressure
  6. customThe crude was purified by CC (Biotage, SNAP 100 g cartridge, solvent A: DCM; solvent B: DCM/MeOH 8:2; gradient in % B: 0 to 5 over 3CV, 5 for 5CV, 5 to 15 over 5CV, 15% B for 3CV)

Sources & evidence

ORD record
ord-566610f4f35340a0b774f7bba81d3d3b
Source dataset
uspto-grants-2016_02
Patent number
US09266876B2

Reaction notes

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