Acetic Acid → HCID 66924240, compound

HRID 1362835Notes

Reaction equation

HRID 1362835 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([NH:14][CH:15]2[CH2:20][CH2:19][N:18]([C:21]3[C:30]([O:31][CH3:32])=[C:29]4[C:24]([C:25](=[O:39])[C:26]([C:36]([OH:38])=[O:37])=[CH:27][N:28]4[CH:33]4[CH2:35][CH2:34]4)=[CH:23][C:22]=3[F:40])[CH2:17][CH2:16]2)[CH2:10][CH2:9]1)=O)(C)(C)C.FC(F)(F)C(O)=O.C(=O)([O-])[O-].[Na+].[Na+].C(O)(=O)C>ClC(Cl)C>[CH:33]1([N:28]2[C:29]3[C:24](=[CH:23][C:22]([F:40])=[C:21]([N:18]4[CH2:19][CH2:20][CH:15]([NH:14][CH:11]5[CH2:12][CH2:13][NH:8][CH2:9][CH2:10]5)[CH2:16][CH2:17]4)[C:30]=3[O:31][CH3:32])[C:25](=[O:39])[C:26]([C:36]([OH:38])=[O:37])=[CH:27]2)[CH2:34][CH2:35]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6422Trifluoroacetic acidHCID 10340Sodium CarbonateHCID 66924231HCID 66924231, compound

Product 1

HCID 66924240HCID 66924240, compound

Reagents, catalysts & solvents 1

HCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of 7-[4-(1-tert-Butoxycarbonyl-piperidin-4-ylamino)-piperidin-1-yl]-1-cyclopropyl-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid (113 mg, 0.2 mmol) in dichloroethane (1.5 mL) was added trifluoroacetic acid (692 mg, 6.07 mmol). The resulting mixture was stirred for 3 hours before condensed to dryness. To this residue was added saturated aqueous sodium carbonate followed by the addition of acetic acid to pH around 6. This aqueous solution was extracted with 20% (v/v) isopropanol/dichloromethane. The combined organic layers were dried over sodium sulfate and condensed to give product as slightly yellow syrup, which was used directly for next reaction. ESI MS m/z 459 (M+H+); 1H NMR (400 MHz, CDCl3) δ 8.74 (s, 1H), 7.78 (d, J=11.6 Hz, 1H), 3.98 (m, 3H), 3.71 (s, 3H), 3.54 (d, J=13.2 Hz, 2H), 3.33 (t, J=13.3 Hz, 2H), 3.14 (m, 1H), 2.91 (d, J=12.5 Hz, 2H), 2.11 (d, J=11.7 Hz, 2H), 2.00 (m, 2H), 1.78 (m, 4H), 1.16 (d, J=7.0 Hz, 2H), 0.93 (d, J=3.3 Hz, 2H).

Workup

  1. extractionThis aqueous solution was extracted with 20% (v/v) isopropanol/dichloromethane
  2. dry with materialThe combined organic layers were dried over sodium sulfate and condensed
  3. customto give product as slightly yellow syrup, which
  4. customwas used directly for next reaction

Sources & evidence

ORD record
ord-1e019b6a62824e0a8d15ad9ae51782fb
Source dataset
uspto-grants-2011_02
Patent number
US07884099B2

Reaction notes

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