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 1292851Notes

Reaction equation

HRID 1292851 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 acidYield 100%

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 washed with brine, dried over sodium sulfate and concentrated in vacuo. The product was isolated 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. washThe combined organic layer was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e9ef7b442b4d42dbbbfe6a4fd56318bc
Source dataset
uspto-grants-2007_07
Patent number
US07238694B2

Reaction notes

Loading…