Hydrochloric Acid → HCID 19876596, compound

HRID 1885964Notes

Reaction equation

HRID 1885964 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[CH3:13][O:14][C:15]1[CH:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([O:23][C:24]2[CH:32]=[CH:31][CH:30]=[CH:29][C:25]=2[C:26]([OH:28])=O)[N:16]=1.[CH3:33][CH:34]([S:36]([NH2:39])(=[O:38])=[O:37])[CH3:35].N12CCCN=C1CCCCC2.Cl>O1CCCC1>[CH3:33][CH:34]([S:36]([NH:39][C:26]([C:25]1[CH:29]=[CH:30][CH:31]=[CH:32][C:24]=1[O:23][C:17]1[N:18]=[C:19]([O:21][CH3:22])[CH:20]=[C:15]([O:14][CH3:13])[N:16]=1)=[O:28])(=[O:38])=[O:37])[CH3:35]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 1841852-((4,6-Dimethoxypyrimidin-2-yl)oxy)benzoic acidHCID 3549191Propane-2-sulfonamide

Product 1

HCID 19876596HCID 19876596, compoundYield 26.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a stirred suspension of 0.33 gram (0.002 mole) of 1,1'-carbonyldiimidazole in 2 mL of tetrahydrofuran was added dropwise a solution of 0.55 gram (0.002 mole) of 2-(4,6-dimethoxypyrimidin-2-yloxy)benzoic acid in 3 mL of tetrahydrofuran. Upon completion of addition, the reaction mixture was stirred at ambient temperature for 30 minutes, and then it was heated to reflux where it was stirred for an additional 30 minutes. After this time the reaction mixture was cooled, and 0.25 gram (0.002 mole) of 1-methylethylsulfonamide (prepared as in Example 1--Step H) was added. Upon completion of addition, the reaction mixture was stirred for 10 minutes, and 0.31 gram (0.002 mole) of 1,8-diazabicyclo[5.4.0]undec-7-ene was added. Upon completion of addition, the reaction mixture was stirred at ambient temperature for five hours. The reaction mixture was then poured into aqueous dilute hydrochloric acid. The mixture was extracted with ethyl acetate, and the extract was dried with magnesium sulfate. The mixture was filtered, and the filtrate was concentrated under reduced pressure to a residue. The residue was subjected to column chromatography on silica gel. Elution was accomplished using 10% and 20% ethyl acetate in methylene chloride. The appropriate fractions were combined and concentrated under reduced pressure to yield 0.2 gram of 2-[2-(1-methylethylsulfonylaminocarbonyl)phenoxy]-4,6-dimethoxypyrimidine; m.p. 128°-130° C., Compound 9 in Table I. The nmr spectrum was consistent with the proposed structure.

Workup

  1. additionUpon completion of addition
  2. temperatureit was heated
  3. temperatureto reflux where it
  4. stirringwas stirred for an additional 30 minutes
  5. temperatureAfter this time the reaction mixture was cooled
  6. additionUpon completion of addition
  7. stirringthe reaction mixture was stirred for 10 minutes
  8. additionUpon completion of addition
  9. stirringthe reaction mixture was stirred at ambient temperature for five hours
  10. extractionThe mixture was extracted with ethyl acetate
  11. dry with materialthe extract was dried with magnesium sulfate
  12. filtrationThe mixture was filtered
  13. concentrationthe filtrate was concentrated under reduced pressure to a residue
  14. washElution
  15. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-a1c59e7352054fd2b8de6b6e149fb649
Source dataset
uspto-grants-1992_09
Patent number
US05149357

Reaction notes

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