Trifluoroacetic acid → 1-Cyclopropyl-6-fluoro-8-methoxy-7-{3-[1-(methyl-piperidin-4-yl-amino)-cyclopropyl]-pyrrolidin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

HRID 1296390Notes

Reaction equation

HRID 1296390 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:43])[C:15]2([CH:18]3[CH2:22][CH2:21][N:20]([C:23]4[C:32]([O:33][CH3:34])=[C:31]5[C:26]([C:27](=[O:41])[C:28]([C:38]([OH:40])=[O:39])=[CH:29][N:30]5[CH:35]5[CH2:37][CH2:36]5)=[CH:25][C:24]=4[F:42])[CH2:19]3)[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O>ClC(Cl)C>[CH:35]1([N:30]2[C:31]3[C:26](=[CH:25][C:24]([F:42])=[C:23]([N:20]4[CH2:21][CH2:22][CH:18]([C:15]5([N:14]([CH3:43])[CH:11]6[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]6)[CH2:17][CH2:16]5)[CH2:19]4)[C:32]=3[O:33][CH3:34])[C:27](=[O:41])[C:28]([C:38]([OH:40])=[O:39])=[CH:29]2)[CH2:37][CH2:36]1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 694924817-(3-{1-[(1-tert-Butoxycarbonyl-piperidin-4-yl)-methyl-amino]-cyclopropyl}-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Product 1

HCID 669244321-Cyclopropyl-6-fluoro-8-methoxy-7-{3-[1-(methyl-piperidin-4-yl-amino)-cyclopropyl]-pyrrolidin-1-yl}-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of 7-(3-{1-[(1-tert-butoxycarbonyl-piperidin-4-yl)-methyl-amino]-cyclopropyl}-pyrrolidin-1-yl)-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid in dichloroethane (2.0 mL) was added trifluoroacetic acid (1.0 mL, ˜13 mmol) at 0° C. during a period of 5-6 minutes. The resulting solution was stirred at room temperature for one hour. The solvent was removed to yield yellow oil, which was partitioned between CH2Cl2 and sat. aq NaHCO3. The separated aqueous phase was extracted with CH2Cl2. The combined organic layer was with brine, dried over sodium sulfate and concentrated in vacuo. Title compound was achieved as a yellow solid (85 mg, 100%). ESI MS m/z 499.4 (M+H+).

Workup

  1. customThe solvent was removed
  2. customto yield yellow oil, which
  3. customwas partitioned between CH2Cl2 and sat. aq NaHCO3
  4. extractionThe separated aqueous phase was extracted with CH2Cl2
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3fefa88ac68b4bee832630c4a86d5310
Source dataset
uspto-grants-2007_07
Patent number
US07247634B2

Reaction notes

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