Cesium carbonate → HCID 66809820, compound

HRID 607264Notes

Reaction equation

HRID 607264 reaction equation
C(OC(=O)[N:7]([C:23]1[C:32]2[C:27](=[N:28][C:29]([S:33][CH2:34][CH3:35])=[N:30][CH:31]=2)[N:26]=[CH:25][N:24]=1)[C:8]1[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=1[S:15][C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=1)(C)(C)C.Br[CH2:38][C:39]#[N:40].C(=O)([O-])[O-].[Cs+].[Cs+]>[I-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C)C=O>[CH2:34]([S:33][C:29]1[N:28]=[C:27]2[N:26]=[CH:25][N:24]=[C:23]([NH:7][C:8]3[CH:13]=[C:12]([CH3:14])[CH:11]=[CH:10][C:9]=3[S:15][C:16]3[CH:17]=[CH:18][C:19]([O:22][CH2:38][C:39]#[N:40])=[CH:20][CH:21]=3)[C:32]2=[CH:31][N:30]=1)[CH3:35]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11534BromoacetonitrileHCID 66808367HCID 66808367, compound

Product 1

HCID 66809820HCID 66809820, compoundYield 20%

Reagents, catalysts & solvents 2

HCID 67553Tetrabutylammonium IodideCatalystHCID 6228DimethylformamideSolvent

Procedure

The product from Example 164 (52 mg, 0.1 mmol), bromo-acetonitrile (0.008 ml, 0.12 mmol), cesium carbonate (0.065 g, 0.2 mmol) and tetrabutylammonium iodide (0.001 g) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 2 hours. The mixture was partitioned between water and ethyl acetate. The organic layer was washed with brine, dried (sodium sulfate), filtered and evaporated under vacuum. To the residue was added dichloromethane (2.5 ml) and trifluoroacetic acid (2.5 ml) then stirred at room temperature for 1 hour. The solvent was evaporated under vacuum and the residue was purified by HPLC with TFA to provide the title compound (9 mg, 20%). 1H NMR (300 MHz, DMSO-D6) δ ppm: 1.42 (t, J=7.35 Hz, 3H), 2.24 (s, 3H), 3.29 (q, J=7.35 Hz, 2H), 5.25 (s, 2H), 6.81 (m, 5H), 7.20 (d, J=8.46 Hz, 2H), 8.34 (s, 1H), 9.25 (s, 1H), 9.75 (s, 1H); MS (ESI+) m/z 461 (M+H)+.

Workup

  1. customThe mixture was partitioned between water and ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried (sodium sulfate)
  4. filtrationfiltered
  5. customevaporated under vacuum
  6. additionTo the residue was added dichloromethane (2.5 ml) and trifluoroacetic acid (2.5 ml)
  7. customThe solvent was evaporated under vacuum
  8. customthe residue was purified by HPLC with TFA

Sources & evidence

ORD record
ord-bfa5a549689d49a693cf8a4d8b18f854
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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