HCID 86680886, compound → HCID 52945927, compound

HRID 1914861Notes

Reaction equation

HRID 1914861 reaction equation
[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]([NH:12][C:13]2[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:14]=2[OH:22])=S)=[CH:5][CH:4]=1)[CH3:2]>C(#N)C>[CH2:1]([C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[O:22][C:14]3[CH:15]=[CH:16][C:17]([N+:19]([O-:21])=[O:20])=[CH:18][C:13]=3[N:12]=2)=[CH:5][CH:4]=1)[CH3:2]

Participants

3

Reactant 1

HCID 86680886HCID 86680886, compound

Product 1

HCID 52945927HCID 52945927, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

In an ice bath under nitrogen gas, 15 mL of acetonitrile was slowly added to KO2 (12.05 mmol, 5 eq) with stirring. Then, the compound (a) synthesized in Example 1 (2.41 mmol, 1 eq) in 20 mL of acetonitrile was slowly added to said solution containing KO2. The mixture was reacted at room temperature for 16 hours, and then the reaction solution was diluted with 30 mL of ice water. This solution was extracted with dichloromethane, and washed two times with saturated aqueous NaCl solution. After drying with anhydrous MgSO4, the precipitate obtained by removing the solvent under reduced pressure was filtered under reduced pressure with EtOAc:hexane=1:10 (V/V) to yield the title compound (b). Yellow powder (88%), mp 172-173° C.; 1H NMR (Acetone-d6, 400 MHz) δ 9.805 (s, 1H), 8.229 (s, 1H), 8.109 (d, J=8.8 Hz, 1H), 7.764 (d, J=8.4 Hz, 2H), 7.615 (d, J=9.2 Hz, 1H), 7.278 (d, J=8.8 Hz, 2H), 2.651 (q, J=7.6 Hz, 2H), 1.230 (t, J=7.6 Hz, 3H).

Workup

  1. additioncontaining KO2
  2. customThe mixture was reacted at room temperature for 16 hours
  3. extractionThis solution was extracted with dichloromethane
  4. washwashed two times with saturated aqueous NaCl solution
  5. dry with materialAfter drying with anhydrous MgSO4
  6. customthe precipitate obtained
  7. customby removing the solvent under reduced pressure
  8. filtrationwas filtered under reduced pressure with EtOAc

Sources & evidence

ORD record
ord-711a3274d2584d4f89c476d1e2828c25
Source dataset
uspto-grants-2013_12
Patent number
US08614240B2

Reaction notes

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