Pyridine → HCID 13017836, compound

HRID 2286214Notes

Reaction equation

HRID 2286214 reaction equation
C(N(CC)CC)C.[OH:8][CH:9]1[N:13]([C:14]2[CH:23]=[CH:22][C:21]3[C:16](=[N:17][C:18]([O:24][CH3:25])=[CH:19][CH:20]=3)[N:15]=2)[C:12](=[O:26])[C:11]2[S:27][CH2:28][CH:29]([O:32][CH3:33])[CH2:30][S:31][C:10]1=2.Cl.Cl[C:36]([N:38]1[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]1)=[O:37].N1C=CC=CC=1>C(Cl)Cl>[CH3:33][O:32][CH:29]1[CH2:30][S:31][C:10]2[C:9](=[O:8])[N:13]([C:14]3[CH:23]=[CH:22][C:21]4[C:16](=[N:17][C:18]([O:24][CH3:25])=[CH:19][CH:20]=4)[N:15]=3)[CH:12]([O:26][C:36]([N:38]3[CH2:43][CH2:42][N:41]([CH3:44])[CH2:40][CH2:39]3)=[O:37])[C:11]=2[S:27][CH2:28]1

Participants

6

Reactant 4

HCID 1049PyridineHCID 8471TriethylamineHCID 30169344-Methylpiperazine-1-carbonyl chloride monohydrochlorideHCID 13017827HCID 13017827, compound

Product 1

HCID 13017836HCID 13017836, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
45 °C

Procedure

Triethylamine (34.5 cc) is added, at about 15° C., to a suspension of 6-hydroxy-3-methoxy-7-(7-methoxy-1,8-naphthyridin-2-yl)-8-oxo-3,4,7,8-tetrahydro-2H,6H-1,4-dithiepino[2,3-c]pyrrole (10.7 g) and 1-chlorocarbonyl-4-methylpiperazine hydrochloride (16.4 g) in anhydrous methylene chloride (440 cc), and anhydrous pyridine (195 cc) is then added to the resulting mixture. The reaction mixture is heated for 3 hours at 45° C. After cooling, the mixture is diluted by adding methylene chloride (300 cc). The organic phase is washed three times with distilled water (total 600 cc), dried over anhydrous sodium sulphate and evaporated. The resulting residue (41.0 g) is treated with boiling methanol (150 cc). After cooling the mixture for 1 hour at 2° C., the crystals are filtered off, washed twice with ice-cooled methanol (total 40 cc) and dried under reduced pressure (20 mm Hg) at 20° C. The resulting product (9.0 g; m.p. 215° C.) is dissolved in boiling methanol (175 cc). After cooling the solution for 2 hours at 2° C., the resulting crystals are filtered off, washed twice with ice-cooled methanol (total 20 cc) and dried under reduced pressure (0.2 mm Hg) at 50° C. 3-Methoxy-7-(7-methoxy-1,8-naphthyridin-2-yl)-6-(4-methylpiperazin-1-yl)carbonyloxy-8-oxo-3,4,7,8-tetrahydro-2H,6H-1,4-dithiepino[2,3-c]pyrrole (7.4 g), melting at 218° 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 distilled water (total 600 cc)
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated
  7. additionThe resulting residue (41.0 g) is treated with boiling methanol (150 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 methanol (total 40 cc)
  12. customdried under reduced pressure (20 mm Hg) at 20° C
  13. dissolutionThe resulting product (9.0 g; m.p. 215° C.) is dissolved
  14. temperatureAfter cooling the solution for 2 hours at 2° C.
  15. filtrationthe resulting crystals are filtered off
  16. washwashed twice with ice-
  17. temperaturecooled methanol (total 20 cc)
  18. customdried under reduced pressure (0.2 mm Hg) at 50° C

Sources & evidence

ORD record
ord-f53523b4666549f5bb5a3d6a2ec79a13
Source dataset
uspto-grants-1982_04
Patent number
US04327095

Reaction notes

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