Trifluoroacetic acid → HCID 21106876, compound

HRID 1765115Notes

Reaction equation

HRID 1765115 reaction equation
C(OC([N:8]1[CH2:13][CH2:12][CH:11]([N:14]([CH3:42])[C:15]2([CH:18]3[CH2:22][CH2:21][N:20]([C:23]4[C:24]([F:41])=[CH:25][N:26]5[C:31]([C:32]=4[CH3:33])=[C:30]([CH:34]4[CH2:36][CH2:35]4)[CH:29]=[C:28]([C:37]([OH:39])=[O:38])[C:27]5=[O:40])[CH2:19]3)[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+]>ClC(Cl)C.CC(O)C.ClCCl>[CH:34]1([C:30]2[CH:29]=[C:28]([C:37]([OH:39])=[O:38])[C:27](=[O:40])[N:26]3[C:31]=2[C:32]([CH3:33])=[C:23]([N:20]2[CH2:21][CH2:22][CH:18]([C:15]4([N:14]([CH3:42])[CH:11]5[CH2:10][CH2:9][NH:8][CH2:13][CH2:12]5)[CH2:16][CH2:17]4)[CH2:19]2)[C:24]([F:41])=[CH:25]3)[CH2:36][CH2:35]1

Participants

7

Reactant 3

HCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 21106878HCID 21106878, compound

Product 1

HCID 21106876HCID 21106876, compoundYield 86.2%

Reagents, catalysts & solvents 3

HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolventHCID 63651,1-DichloroethaneSolvent

Procedure

To a stirred solution of 8-(3-{1-[(1-tert-butoxycarbonyl-piperidin-4-yl)-methyl-amino]-cyclopropyl}-pyrrolidin-1-yl)-1-cyclopropyl-7-fluoro-9-methyl-4-oxo-4H-quinolizine-3-carboxylic acid (14 g) in dichloroethane (100 mL) was added trifluoroacetic acid (30 mL) at 0° C. slowly. The resulting solution was stirred at 0° C. to room temperature for one hour. The solvent was removed in vacuo to yield yellow oil, which was dissolved in 20% IPA in dichloromethane and the solution was neutralized by sat. aq NaHCO3 resulting two clear phases, and the two phases were well shaken. The organic layer was separated, and the aqueous phase was extracted with 20% IPA/CH2Cl2. The combined organic extracts were washed with brine, dried over sodium sulfate and concentrated in vacuo to give yellow solid (10 g), the solid was crystallized from methanol/water to give crystalline solid (8 g). ESI MS m/z 483.3 (M+H+). 1H NMR (400 MHz, CD3OD) δ 8.88 (d, J=10.0 Hz, 1H), 7.93 (s, 1H), 4.03-3.98 (m, 1H), 3.79-3.75 (m, 1H), 3.66-3.62 (m, 1H), 3.58-3.52(m, 1H), 3.47-3.44 (m, 2H), 3.05-2.88 (m, 4H), 2.62 (s, 3H), 2.49 (s, 3H), 2.35-2.23 (m, 3H), 2.06-2.02 (m, 1H), 1.70-1.58 (m, 2H), 1.51-1.44 (m, 1H), 0.93-0.64 (m, 8H).

Workup

  1. customThe solvent was removed in vacuo
  2. customto yield yellow oil, which
  3. stirringthe two phases were well shaken
  4. customThe organic layer was separated
  5. extractionthe aqueous phase was extracted with 20% IPA/CH2Cl2
  6. washThe combined organic extracts were washed with brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-af5fe383ff504fd8aeb0a084a47ed6f8
Source dataset
uspto-grants-2007_06
Patent number
US07226931B2

Reaction notes

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