7-[4-[2-(n-Benzyl-n-methylamino)-1-chloroethylidene]piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid trifluoroacetic acid salt → 1-Cyclopropyl-6-fluoro-8-methoxy-7-[4-(2-methylamino-ethylidene)-piperidin-1-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid trifluoroacetic acid salt

HRID 15506Notes

Reaction equation

HRID 15506 reaction equation
[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH2:8]([N:15]([CH2:17][C:18](=[C:20]1[CH2:25][CH2:24][N:23]([C:26]2[C:35]([O:36][CH3:37])=[C:34]3[C:29]([C:30](=[O:44])[C:31]([C:41]([OH:43])=[O:42])=[CH:32][N:33]3[CH:38]3[CH2:40][CH2:39]3)=[CH:28][C:27]=2[F:45])[CH2:22][CH2:21]1)Cl)C)C1C=CC=CC=1>CO.C(O)=O.[Pd]>[F:1][C:2]([F:7])([F:6])[C:3]([OH:5])=[O:4].[CH:38]1([N:33]2[C:34]3[C:29](=[CH:28][C:27]([F:45])=[C:26]([N:23]4[CH2:24][CH2:25][C:20](=[CH:18][CH2:17][NH:15][CH3:8])[CH2:21][CH2:22]4)[C:35]=3[O:36][CH3:37])[C:30](=[O:44])[C:31]([C:41]([OH:43])=[O:42])=[CH:32]2)[CH2:39][CH2:40]1

Participants

4

Reactant 1

HCID 686897667-[4-[2-(n-Benzyl-n-methylamino)-1-chloroethylidene]piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid trifluoroacetic acid salt

Product 1

HCID 686924641-Cyclopropyl-6-fluoro-8-methoxy-7-[4-(2-methylamino-ethylidene)-piperidin-1-yl]-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid trifluoroacetic acid saltYield 15%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 18963719Formic acid methanolSolvent

Procedure

A solution of 161 (70 mg, 0.11 mmol) in methanol/formic acid (v/v=20/1) (14 mL) was treated with 10% Pd/C (35 mg, 7.3 mmol) under nitrogen at rt and stirred for 3 h. The resulting mixture was filtered and concentrated in vacuo. The residue was purified by HPLC (reverse phase C-18 column, 35-90% acetonitrile/water containing 0.1% trifluoroacetic acid) to afford the trifluoroacetic acid salt of 221 (8.3 mg, 15%) as a yellow solid. MS 416 (M+H).

Workup

  1. filtrationThe resulting mixture was filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was purified by HPLC (reverse phase C-18 column, 35-90% acetonitrile/water containing 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-d8d84525491b41ad84594ab336ea1579
Source dataset
uspto-grants-2010_06
Patent number
US07732612B2

Reaction notes

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