Formaldehyde → 5-[2-(Isopropyloxycarbonylamino)ethylthio]-3-morpholinomethylimidazo[1,2-a]pyridine

HRID 5485Notes

Reaction equation

HRID 5485 reaction equation
[CH2:1]=O.[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[CH:9]([O:12][C:13]([NH:15][CH2:16][CH2:17][S:18][C:19]1[N:24]2[CH:25]=[CH:26][N:27]=[C:23]2[CH:22]=[CH:21][CH:20]=1)=[O:14])([CH3:11])[CH3:10]>C(O)(=O)C>[CH:9]([O:12][C:13]([NH:15][CH2:16][CH2:17][S:18][C:19]1[N:24]2[C:25]([CH2:1][N:3]3[CH2:8][CH2:7][O:6][CH2:5][CH2:4]3)=[CH:26][N:27]=[C:23]2[CH:22]=[CH:21][CH:20]=1)=[O:14])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 8083MorpholineHCID 233628125-[2-(Isopropyloxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine

Product 1

HCID 233628355-[2-(Isopropyloxycarbonylamino)ethylthio]-3-morpholinomethylimidazo[1,2-a]pyridineYield 50.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of an aqueous 37% formalin solution (210 mg, 2.59 mmoles) in acetic acid (2 ml) was added morpholine (226 μl, 2.59 mmoles) under ice-cooling and the mixture was stirred at room temperature for 45 minutes. 5-[2-(isopropyloxycarbonylamino)ethylthio]imidazo[1,2-a]pyridine (651 mg, 2.33 mmoles) was added, followed by stirring at 60° C. for 2 hours. After the solvent was distilled off, the residue was diluted with chloroform, washed in turn with aqueous 1N NaOH and saturated saline, and then dried over anhydrous magnesium sulfate. After the solvent was distilled off, the residue was purified by column chromatography [eluent: ethanol/ethyl acetate=1:10] to obtain 442 mg of the desired product (50.1%, light brown solid).

Workup

  1. temperaturecooling
  2. stirringby stirring at 60° C. for 2 hours
  3. distillationAfter the solvent was distilled off
  4. additionthe residue was diluted with chloroform
  5. washwashed in turn with aqueous 1N NaOH and saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationAfter the solvent was distilled off
  8. customthe residue was purified by column chromatography [eluent: ethanol/ethyl acetate=1:10]

Sources & evidence

ORD record
ord-9e25ae07e399492788ca461ed5c581a2
Source dataset
uspto-grants-1993_09
Patent number
US05244908

Reaction notes

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