Pyridine → HCID 13017831, compound

HRID 2286212Notes

Reaction equation

HRID 2286212 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH:19]([OH:20])[C:18]3[S:21][CH2:22][CH:23]([O:26][CH3:27])[CH2:24][S:25][C:17]=3[C:16]2=[O:28])=[N:13][CH:14]=1.Cl.Cl[C:31]([N:33]1[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]1)=[O:32].N1C=CC=CC=1>C(Cl)Cl>[Cl:8][C:9]1[CH:10]=[CH:11][C:12]([N:15]2[CH:16]([O:28][C:31]([N:33]3[CH2:38][CH2:37][N:36]([CH3:39])[CH2:35][CH2:34]3)=[O:32])[C:17]3[S:25][CH2:24][CH:23]([O:26][CH3:27])[CH2:22][S:21][C:18]=3[C:19]2=[O:20])=[N:13][CH:14]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochlorideHCID 13017825HCID 13017825, compound

Product 1

HCID 13017831HCID 13017831, compoundYield 31.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

Triethylamine (42 cc) is added, at about 15° C., to a suspension of 7-(5-chloropyrid-2-yl)-6-hydroxy-3-methoxy-8-oxo-3,4,7,8-tetrahydro-2H,6H-1,4-dithiepino[2,3-c]pyrrole (7.4 g) and 1-chlorocarbonyl-4-methylpiperazine hydrochloride (43.0 g) in anhydrous methylene chloride (215 cc), and anhydrous pyridine (90 cc) is then added to the resulting mixture. The reaction mixture is heated for 10 hours at 45° C. After cooling, the mixture is diluted by adding methylene chloride (250 cc). The organic phase is washed three times with an N aqueous sodium hydroxide solution (total 300 cc) and three times with distilled water (total 750 cc), dried over anhydrous sodium sulphate and evaporated. The residue is dissolved in boiling ethanol (50 cc). After cooling the solution for 20 hours at 2° C., the resulting crystals are filtered off, washed three times with ice-cooled ethanol (total 30 cc) and dried under reduced pressure (20 mm Hg). The resulting product (5.1 g; m.p. 197° C.) is dissolved in boiling ethanol (80 cc). After filtering the boiling solution and then cooling the filtrate for 16 hours at 2° C., the resulting crystals are filtered off, washed with ice-cooled ethanol (8 cc) and dried under reduced pressure (0.2 mm Hg) at 55° C. 7-(5-Chloropyrid-2-yl)-3-methoxy-6-(4-methylpiperazin-1-yl)carbonyloxy-8-oxo-3,4,7,8-tetrahydro-2H,6H-1,4-dithiepino[2,3-c]-pyrrole (3.2 g), which melts at 199° C., is obtained.

Workup

  1. additionis then added to the resulting mixture
  2. temperatureAfter cooling
  3. additionthe mixture is diluted
  4. washThe organic phase is washed three times with an N aqueous sodium hydroxide solution (total 300 cc) and three times with distilled water (total 750 cc)
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. dissolutionThe residue is dissolved
  8. temperatureAfter cooling the solution for 20 hours at 2° C.
  9. filtrationthe resulting crystals are filtered off
  10. washwashed three times with ice-
  11. temperaturecooled ethanol (total 30 cc)
  12. customdried under reduced pressure (20 mm Hg)
  13. dissolutionThe resulting product (5.1 g; m.p. 197° C.) is dissolved
  14. filtrationAfter filtering the boiling solution
  15. temperaturecooling the filtrate for 16 hours at 2° C.
  16. filtrationthe resulting crystals are filtered off
  17. washwashed with ice-
  18. temperaturecooled ethanol (8 cc)
  19. customdried under reduced pressure (0.2 mm Hg) at 55° C

Sources & evidence

ORD record
ord-db562d66f1fd4c409f4f035d546927bd
Source dataset
uspto-grants-1982_04
Patent number
US04327095

Reaction notes

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