Potassium Carbonate → HCID 70792421, compound

HRID 2405036Notes

Reaction equation

HRID 2405036 reaction equation
[CH2:1]([O:8][C:9](=[O:29])[NH:10][CH2:11][C:12](=[O:28])[NH:13][C:14]1[C:18]([C:19]2[NH:23][C:22]3[CH:24]=[CH:25][CH:26]=[CH:27][C:21]=3[N:20]=2)=[N:17][O:16][N:15]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:36]([O:43][C:44](=[O:56])[NH:45][C:46]1[CH:51]=[CH:50][C:49]([C:52](=[O:55])[CH2:53]Br)=[CH:48][CH:47]=1)[C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1>CN(C=O)C.C(OCC)(=O)C>[CH2:36]([O:43][C:44](=[O:56])[NH:45][C:46]1[CH:47]=[CH:48][C:49]([C:52](=[O:55])[CH2:53][N:20]2[C:21]3[CH:27]=[CH:26][CH:25]=[CH:24][C:22]=3[N:23]=[C:19]2[C:18]2[C:14]([NH:13][C:12](=[O:28])[CH2:11][NH:10][C:9]([O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)=[O:29])=[N:15][O:16][N:17]=2)=[CH:50][CH:51]=1)[C:37]1[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 18981260Benzyl [4-(bromoacetyl)phenyl]carbamateHCID 136352173HCID 136352173, compound

Product 1

HCID 70792421HCID 70792421, compoundYield 31.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a stirred solution of 0.4 g of {[4-(1H-benzoimidazol-2-yl)-furazan-3-ylcarbamoyl]-methyl}-carbamic acid benzyl ester (0.97 mmol, 1 eq.) in 6 mL of N,N′-dimethylformamide are added 0.2 g of potassium carbonate (1.4 mmol; 1.45 eq.) at room temperature followed by the addition of 0.41 g of [4-(2-bromo-acetyl)-phenyl]-carbamic acid benzyl ester (CAS 157014-41-0) (1.16 mmol; 1.2 eq.). The reaction mixture is stirred for 2 h at room temperature and is then diluted with 20 mL of ethyl acetate. The solution is washed with water (2×10 mL) and brine (2×10 mL), dried over magnesium sulfate, filtered and concentrated to dryness under reduced pressure. The residue is then dissolved in hot ethyl acetate (2 mL) and the solution is placed in an ice-bath. After 0.5 h, the resulting suspension is filtered and the solid is washed with cold ethyl acetate (1 mL) to afford 0.2 g of the desired product as a white powder.

Workup

  1. washThe solution is washed with water (2×10 mL) and brine (2×10 mL)
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. dissolutionThe residue is then dissolved in hot ethyl acetate (2 mL)
  6. customthe solution is placed in an ice-bath
  7. waitAfter 0.5 h
  8. filtrationthe resulting suspension is filtered
  9. washthe solid is washed with cold ethyl acetate (1 mL)

Sources & evidence

ORD record
ord-28450c942a5240af925c2164ae105cfb
Source dataset
uspto-grants-2014_08
Patent number
US08802858B2

Reaction notes

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