Pyridine → HCID 13017832, compound

HRID 2286213Notes

Reaction equation

HRID 2286213 reaction equation
C(N(CC)CC)C.[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([N:19]3[CH:23]([OH:24])[C:22]4[S:25][CH2:26][CH:27]([O:30][CH3:31])[CH2:28][S:29][C:21]=4[C:20]3=[O:32])=[N:16]2)=[CH:11][CH:10]=1.Cl.Cl[C:35]([N:37]1[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]1)=[O:36].N1C=CC=CC=1>C(Cl)Cl>[Cl:8][C:9]1[CH:18]=[C:17]2[C:12]([CH:13]=[CH:14][C:15]([N:19]3[CH:20]([O:32][C:35]([N:37]4[CH2:42][CH2:41][N:40]([CH3:43])[CH2:39][CH2:38]4)=[O:36])[C:21]4[S:29][CH2:28][CH:27]([O:30][CH3:31])[CH2:26][S:25][C:22]=4[C:23]3=[O:24])=[N:16]2)=[CH:11][CH:10]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochlorideHCID 20542233HCID 20542233, compound

Product 1

HCID 13017832HCID 13017832, compoundYield 41.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

Triethylamine (29.5 cc) is added, at about 15° C., to a suspension of 7-(7-chloroquinol-2-yl)-6-hydroxy-3-methoxy-8-oxo-3,4,7,8-tetrahydro-2H,6H-1,4-dithiepino[2,3-c]pyrrole (6.0 g) and 1-chlorocarbonyl-4-methylpiperazine hydrochloride (30.2 g) in anhydrous methylene chloride (150 cc), and anhydrous pyridine (65 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 (300 cc). The organic phase is washed twice with an N aqueous sodium hydroxide solution (total 600 cc) and five times with distilled water (total 1000 cc), dried over sodium sulphate and evaporated. The residue is treated with boiling ethanol (50 cc). After cooling the mixture for 1 hour at 2° C., the crystals are filtered off, washed twice with ice-cooled ethanol (total 20 cc) and dried under reduced pressure (20 mm Hg). The resulting product (4.6 g; m.p. 228° C.) is dissolved in a boiling mixture of acetonitrile (50 cc) and ethanol (150 cc). After cooling the solution for 16 hours at 2° C., the resulting crystals are filtered off, washed with ice-cooled ethanol (5 cc) and dried under reduced pressure (0.2 mm Hg) at 55° C. 7-(7-Chloroquinol-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 (3.3 g), melting at 228° 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 twice with an N aqueous sodium hydroxide solution (total 600 cc) and five times with distilled water (total 1000 cc)
  5. dry with materialdried over sodium sulphate
  6. customevaporated
  7. additionThe residue is treated with boiling ethanol (50 cc)
  8. temperatureAfter cooling the mixture for 1 hour at 2° C.
  9. filtrationthe crystals are filtered off
  10. washwashed twice with ice-
  11. temperaturecooled ethanol (total 20 cc)
  12. customdried under reduced pressure (20 mm Hg)
  13. dissolutionThe resulting product (4.6 g; m.p. 228° C.) is dissolved in a boiling mixture of acetonitrile (50 cc) and ethanol (150 cc)
  14. temperatureAfter cooling the solution for 16 hours at 2° C.
  15. filtrationthe resulting crystals are filtered off
  16. washwashed with ice-
  17. temperaturecooled ethanol (5 cc)
  18. customdried under reduced pressure (0.2 mm Hg) at 55° C

Sources & evidence

ORD record
ord-5e38e2404c504064bf0150feca523b8c
Source dataset
uspto-grants-1982_04
Patent number
US04327095

Reaction notes

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