Pyridine → HCID 21438293, compound

HRID 2397446Notes

Reaction equation

HRID 2397446 reaction equation
C(N(CC)CC)C.N1C=CC=CC=1.[OH:14][CH:15]1[N:19]([C:20]2[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=2)[C:18](=[O:27])[C:17]2[O:28][CH2:29][CH2:30][S:31][C:16]1=2.Cl.Cl[C:34]([N:36]1[CH2:41][CH2:40][N:39]([CH3:42])[CH2:38][CH2:37]1)=[O:35]>C(Cl)Cl.O>[CH3:42][N:39]1[CH2:40][CH2:41][N:36]([C:34]([O:14][CH:15]2[N:19]([C:20]3[CH:25]=[CH:24][C:23]([CH3:26])=[CH:22][N:21]=3)[C:18](=[O:27])[C:17]3[O:28][CH2:29][CH2:30][S:31][C:16]2=3)=[O:35])[CH2:37][CH2:38]1

Participants

7

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochlorideHCID 21438302HCID 21438302, compound

Product 1

HCID 21438293HCID 21438293, compoundYield 65.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

Triethylamine (6.2 cc.) followed by anhydrous pyridine (27.5 cc.) is added to a suspension of 5-hydroxy-6-(5-methylpyrid-2-yl)-7-oxo-2,3,6,7-tetrahydro-5H-1,4-oxathiino[2,3-c]pyrrole (2.9 g.) and 1-chlorocarbonyl-4-methylpiperazine hydrochloride (6.6 g.) in methylene chloride (55 cc.). The reaction mixture is then heated under reflux for 6 hours. After cooling, water (150 cc.) and methylene chloride (50 cc.) are added. The aqueous phase is decanted and washed with methylene chloride (50 cc.). The organic phases are combined and washed by decanting successively with water (2 × 50 cc.), N aqueous sodium hydroxide solution (50 cc.) and water (2 × 50 cc.). After drying over sodium sulphate and treatment with decolourising charcoal, the organic phase is evaporated to dryness under reduced pressure. Recrystallisation of the residue from acetonitrile (40 cc.) gives 5-(4-methylpiperazin-1-yl)carbonyloxy-6-(5-methylpyrid-2-yl)-7-oxo-2,3,6,7-tetrahydro-5H-1,4-oxathiino[2,3-c]pyrrole (2.8 g.) melting at 183° C.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureunder reflux for 6 hours
  3. temperatureAfter cooling
  4. customThe aqueous phase is decanted
  5. washwashed with methylene chloride (50 cc.)
  6. washwashed
  7. customby decanting successively with water (2 × 50 cc.), N aqueous sodium hydroxide solution (50 cc.) and water (2 × 50 cc.)
  8. dry with materialAfter drying over sodium sulphate and treatment with decolourising charcoal
  9. customthe organic phase is evaporated to dryness under reduced pressure
  10. customRecrystallisation of the residue from acetonitrile (40 cc.)

Sources & evidence

ORD record
ord-8f8e1737982c48b09ffb52bc94548b76
Source dataset
uspto-grants-1977_05
Patent number
US04021554

Reaction notes

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