Hydrochloric Acid → HCID 86709407, compound

HRID 2172273Notes

Reaction equation

HRID 2172273 reaction equation
C(N(CC)CC)C.[N+:8]([C:11]1[N:12]=[C:13]2[N:18]([CH:19]=1)[CH2:17][CH2:16][C@H:15]([CH2:20][O:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]3[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=1)[O:14]2)([O-:10])=[O:9].[CH3:34][S:35](Cl)(=[O:37])=[O:36].Cl>C(Cl)Cl>[CH3:34][S:35]([N:31]1[CH2:32][CH2:33][N:28]([C:25]2[CH:26]=[CH:27][C:22]([O:21][CH2:20][C@@H:15]3[O:14][C:13]4=[N:12][C:11]([N+:8]([O-:10])=[O:9])=[CH:19][N:18]4[CH2:17][CH2:16]3)=[CH:23][CH:24]=2)[CH2:29][CH2:30]1)(=[O:37])=[O:36]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 70874384HCID 70874384, compound

Product 1

HCID 86709407HCID 86709407, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (0.31 ml) was added to a methylene chloride suspension (6 ml) of (R)-2-nitro-7-(4-piperazin-1-ylphenoxymethyl)-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (0.40 g). Subsequently, methanesulfonyl chloride (0.09 ml) was added thereto dropwise under ice cooling, and the mixture was stirred for 14 hours while it gradually returned to room temperature. A 0.5 N hydrochloric acid aqueous solution was added to the reaction mixture, followed by extraction with methylene chloride. The organic layer was washed with water and a saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate, and the solvent was then distilled off under reduced pressure. The resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=90:10) and recrystallized from methylene chloride-methanol to afford the title compound as a beige powder (0.15 g).

Workup

  1. customgradually returned to room temperature
  2. extractionfollowed by extraction with methylene chloride
  3. washThe organic layer was washed with water
  4. dry with materiala saturated sodium chloride aqueous solution, dried over anhydrous sodium sulfate
  5. distillationthe solvent was then distilled off under reduced pressure
  6. customThe resulting residue was purified by silica gel column chromatography (methylene chloride:methanol=90:10)
  7. customrecrystallized from methylene chloride-methanol

Sources & evidence

ORD record
ord-161463910a15421c9bce70c1cb751b0c
Source dataset
uspto-grants-2015_06
Patent number
US09051333B2

Reaction notes

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