Cesium carbonate → HCID 22458348, compound

HRID 2184917Notes

Reaction equation

HRID 2184917 reaction equation
[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([NH:21][C:22](=[O:35])/[C:23](/[F:34])=[C:24](\[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=2)/[CH3:25])=[CH:17][CH:16]=1)(=[O:8])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[Cs+].[Cs+].[C:42]([O:45][CH2:46]Br)(=[O:44])[CH3:43]>CN(C=O)C.C(OCC)(=O)C>[C:1]([NH:5][S:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[CH:20]=[CH:19][C:18]([N:21]([C:22](=[O:35])/[C:23](/[F:34])=[C:24](\[C:26]2[CH:31]=[CH:30][CH:29]=[C:28]([C:32]#[N:33])[CH:27]=2)/[CH3:25])[CH2:43][C:42]([O:45][CH3:46])=[O:44])=[CH:17][CH:16]=1)(=[O:7])=[O:8])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 68536Bromomethyl acetateHCID 22458355HCID 22458355, compound

Product 1

HCID 22458348HCID 22458348, compoundYield 86.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (2E)-N-[4-(2-{[(tert-butyl)amino]sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-fluorobut-2-enamide (230 mg, 0.47 mmol) in 15 ml DMF was added cesium carbonate (460 mg, 1.41 mmol) and bromomethyl acetate (355 mg, 2.35 mmol). The reaction mixture was stirred at room temperature for 4 hours then diluted with 25 ml of ethyl acetate. Organic was washed with 3×25 ml water, 3×25 ml saturated brine solution, dried over magnesium sulfate, filtered and concentrated in vacuo to give methyl 2-{(2E)-N-[4-(2-{[(tert-butyl)amino]-sulfonyl}phenyl)phenyl]-3-(3-cyanophenyl)-2-fluorobut-2-enoylamino}acetate (230 mg, 86%) as yellow foam. ES-MS (M+H+): 563.2.

Workup

  1. washOrganic was washed with 3×25 ml water, 3×25 ml saturated brine solution
  2. dry with materialdried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3861803f899483db79df10a20cde48b
Source dataset
uspto-grants-2002_06
Patent number
US06399627B1

Reaction notes

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