N-methyl-2-pyrrolidone → Moxifloxacin

HRID 1766108Notes

Reaction equation

HRID 1766108 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:17])=[C:11](F)[C:12]=3[O:14][CH3:15])[C:7](=[O:18])[CH:6]([C:19]([OH:21])=[O:20])[C:5]2=O)[CH2:3][CH2:2]1.C[N:24]1[CH2:28][CH2:27][CH2:26][C:25]1=O>C(O)(C)C>[CH3:15][O:14][C:12]1[C:11]([N:24]2[CH2:25][C@@H:26]3[C@@H:27]([CH2:3][CH2:2][CH2:1][NH:4]3)[CH2:28]2)=[C:10]([F:17])[CH:9]=[C:8]2[C:7]([C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]([CH:1]3[CH2:3][CH2:2]3)[C:13]=12)=[O:18]

Participants

4

Reactant 2

HCID 13387N-methyl-2-pyrrolidoneHCID 211100191-Cyclopropyl-6,7-difluoro-1,2,3,4-tetrahydro-8-methoxy-2,4-dioxo-3-quinolinecarboxylic acid

Product 1

HCID 152946Moxifloxacin

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxo-8-methoxy quinolone-3-carboxylic acid (100 grams), (S,S) Diazabicyclo nonane (60 grams) and 1,8-Diazabicyclo[5.4.0.]undec-7-ene(DBU) (10.gms) were added to N-Methylpyrolidinone (250 ml) and the reaction mixture was slowly heated to the 60–70° C. temperature and stirred till the reaction was substantially completed. 5% aqueous isopropyl alcohol was added to the reaction mass, and pH was adjusted towards basic with caustic lye. Then the reaction mass was filtered, through clarifying filter, washed with 5% aqueous isopropyl alcohol. Combined total filtrate and adjusted pH to 7.0 to 7.2 with aqueous Hcl. and isolated at a temperature of 10–15° C. to afford moxifloxacin. Moxifloxacin then treated with Hydrochloric acid in 10% aqueous methanol to yield corresponding hydrochloride salt. (Wet weight: 115 grams)

Workup

  1. temperaturethe reaction mixture was slowly heated to the 60–70° C. temperature
  2. filtrationThen the reaction mass was filtered
  3. filtrationthrough clarifying filter
  4. washwashed with 5% aqueous isopropyl alcohol
  5. customand isolated at a temperature of 10–15° C.

Sources & evidence

ORD record
ord-1d34a37d249e464994083d93550df307
Source dataset
uspto-grants-2007_06
Patent number
US07230006B2

Reaction notes

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