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Dimethyl Sulfoxide → Gatifloxacin

HRID 30450
Notes
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Reaction equation

HRID 30450 reaction equation
CS(C)=O.CC1CNCCN1.[CH3:12][CH:13]1[NH:18][CH2:17][CH2:16][N:15]([C:19]2[C:24]([O:25][CH3:26])=[C:23]3[N:27]([CH:35]4[CH2:37][CH2:36]4)[CH:28]=[C:29]([C:32]([OH:34])=[O:33])[C:30](=[O:31])[C:22]3=[CH:21][C:20]=2[F:38])[CH2:14]1.Cl>O>[CH3:12][CH:13]1[NH:18][CH2:17][CH2:16][N:15]([C:19]2[C:24]([O:25][CH3:26])=[C:23]3[N:27]([CH:35]4[CH2:37][CH2:36]4)[CH:28]=[C:29]([C:32]([OH:34])=[O:33])[C:30](=[O:31])[C:22]3=[CH:21][C:20]=2[F:38])[CH2:14]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 660572-MethylpiperazineHCID 17956339Gatifloxacin hydrochloride

Product 1

HCID 5379Gatifloxacin

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
48 °C

Procedure

A 140 liter reactor equipped with mechanical stirrer, condenser and thermometer, was charged with dimethyl sulfoxide (DMSO, 120 L). The DMSO was heated to 55° C. and the reactor was charged with 2-methylpiperazine (8.6 kg). Gatifloxacin acid was charged, in four portions, every 2 hours (3×4=12 Kg). The reaction mixture was stirred at a rate of 110 rpm under nitrogen atmosphere. The temperature was maintained for 24 hours until completion of the reaction. The reaction mixture was cooled to 48° C. and water (24 L) was added at this temperature. The mixture was cooled to 5° C. during 3.5 hours and maintained with stirring for 15 hours at this temperature. The mixture was filtered (suction) and washed with acetonitrile (18 L) to obtain 15.9 Kg of gatifloxacin.

Workup

  1. customA 140 liter reactor equipped with mechanical stirrer, condenser
  2. temperatureThe temperature was maintained for 24 hours until completion of the reaction
  3. temperatureThe mixture was cooled to 5° C. during 3.5 hours
  4. temperaturemaintained
  5. stirringwith stirring for 15 hours at this temperature
  6. filtrationThe mixture was filtered (suction)
  7. washwashed with acetonitrile (18 L)

Sources & evidence

ORD record
ord-008428864d23457fbaa80699c21184b4
Source dataset
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07423153B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes