Water → HCID 91583876, compound

HRID 404932Notes

Reaction equation

HRID 404932 reaction equation
[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[N:19]=[C:18]([CH:20]([NH2:22])[CH3:21])[O:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:3])[CH3:2].C([O-])([O-])=O.[K+].[K+].[C:31]([O:34][CH2:35]Br)(=[O:33])[CH3:32].O>CC#N.C(OCC)(=O)C>[CH:1]([O:4][C:5]1[CH:24]=[CH:23][C:8]([O:9][C:10]2[S:11][C:12]([C:15]3[N:19]=[C:18]([CH:20]([NH:22][CH2:32][C:31]([O:34][CH3:35])=[O:33])[CH3:21])[O:17][N:16]=3)=[CH:13][N:14]=2)=[CH:7][CH:6]=1)([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 68536Bromomethyl acetateHCID 23648838HCID 23648838, compound

Product 1

HCID 91583876HCID 91583876, compoundYield 24.5%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of Example 40D (100 mg, 0.22 mmol) in CH3CN (1.0 mL) was added K2CO3 (150 mg, 1.1 mmol) and bromomethyl acetate (20 μL, 0.22 mmol). The reaction solution was heated to reflux with stirring for 2 hours, cooled, diluted with ethyl acetate and poured into water. The organics were separated, dried (Na2SO4), filtered and concentrated by rotary evaporation. The residue was purified by reverse phase HPLC (water:acetonitrile; gradient of 5% to 90% acetonitrile) to provide the title compound (23 mg, 0.054 mmol, 24%). MS (ESI APCI) m/z 419.19 (M+H+); 1H NMR (300 MHz, DMSO-d6) δ 8.01 (s, 1H) 7.37 (d, J=8.82 Hz, 2H) 7.04 (d, J=9.19 Hz, 2H) 4.57-4.72 (m, 2H) 3.83 (bs, 2H) 3.66 (s, 3H) 1.57 (d, J=6.99 Hz, 3H) 1.29 (d, J=6.25 Hz, 6H).

Workup

  1. temperatureThe reaction solution was heated
  2. temperatureto reflux
  3. temperaturecooled
  4. customThe organics were separated
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated by rotary evaporation
  8. customThe residue was purified by reverse phase HPLC (water:acetonitrile; gradient of 5% to 90% acetonitrile)

Sources & evidence

ORD record
ord-eef651e375864505bd1e3081f1604e6b
Source dataset
uspto-grants-2014_06
Patent number
US08748627B2

Reaction notes

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