Triethylamine → 7-(trans-3-Amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

HRID 358866Notes

Reaction equation

HRID 358866 reaction equation
C[O-].[Na+].[ClH:4].Cl.[NH2:6][C@H:7]1[C@H:11]([O:12][CH3:13])[CH2:10][NH:9][CH2:8]1.[CH:14]1([N:17]2[C:26]3[C:21](=[CH:22][C:23]([F:30])=[C:24](F)[C:25]=3[O:27][CH3:28])[C:20](=[O:31])[C:19]([C:32]([OH:34])=[O:33])=[CH:18]2)[CH2:16][CH2:15]1.[B](F)F.C(N(CC)CC)C>CS(C)=O.O>[ClH:4].[NH2:6][C@H:7]1[C@H:11]([O:12][CH3:13])[CH2:10][N:9]([C:24]2[C:25]([O:27][CH3:28])=[C:26]3[C:21]([C:20](=[O:31])[C:19]([C:32]([OH:34])=[O:33])=[CH:18][N:17]3[CH:14]3[CH2:16][CH2:15]3)=[CH:22][C:23]=2[F:30])[CH2:8]1

Participants

8

Reactant 5

HCID 8471TriethylamineHCID 139622Boron difluorideHCID 70194651-Cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxo-3-quinolinecarboxylic acidHCID 10942334Sodium MethoxideHCID 67925434trans-3-Amino-4-methoxypyrrolidine dihydrochloride

Product 1

HCID 679254237-(trans-3-Amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

0.19 g (0.0036 mole) of sodium methoxide was added to a suspension of 0.34 g (0.0018 mole) of trans-3-amino-4-methoxypyrrolidine dihydrochloride (prepared as described in Preparation 18) in 1.5 ml of dimethyl sulfoxide, and the mixture was stirred at room temperature for 30 minutes. 0.31 g (0.0009 mole) of a chelate (IV) of 1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and boron difluoride (prepared as described in Preparation 7) were added to the resulting solution, followed by 0.27 g (0.0027 mole) of triethylamine. The mixture was then allowed to stand at room temperature overnight. At the end of this time, 50 ml of water were added to the mixture, and a chelate (V) separated out. This was collected by filtration to give yellow crystals. These were worked up in a similar manner to that described in Example 22, to give 0.22 g of 7-(trans-3-amino-4-methoxy-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-8-methoxy-1,4 -dihydro-4-oxoquinoline-3-carboxylic acid hydrochloride as a fine yellow powder, melting at 192°-195° C.

Workup

  1. waitto stand at room temperature overnight
  2. customa chelate (V) separated out
  3. filtrationThis was collected by filtration
  4. customto give yellow crystals

Sources & evidence

ORD record
ord-eca6fc79925a4672b9db5fc69cf38e23
Source dataset
uspto-grants-1991_03
Patent number
US04997943

Reaction notes

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