1-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl Ester → HCID 54487111, compound

HRID 846698Notes

Reaction equation

HRID 846698 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([F:19])[C:11](F)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:20]2[CH2:22][CH2:21]2)[CH:7]=1)=[O:5])[CH3:2].[NH2:23][CH:24]1[C:28]2([O:32][CH2:31][CH2:30][O:29]2)[CH2:27][NH:26][CH2:25]1>C(Cl)Cl>[CH2:1]([O:3][C:4]([C:6]1[C:15](=[O:16])[C:14]2[C:9](=[C:10]([F:19])[C:11]([N:26]3[CH2:25][CH:24]([NH2:23])[C:28]4([O:32][CH2:31][CH2:30][O:29]4)[CH2:27]3)=[C:12]([F:17])[CH:13]=2)[N:8]([CH:20]2[CH2:22][CH2:21]2)[CH:7]=1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 5354151-Cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic Acid Ethyl EsterHCID 19883306HCID 19883306, compound

Product 1

HCID 54487111HCID 54487111, compoundYield 44.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Following the procedure of Step 1 Example 80, starting with 0.750 g (2.4 mmol) of 1-cyclopropyl-6,7,8-trifluoro-1,4-dihydro-4-oxo-3-quinolinecarboxylic acid ethyl ester and substituting 0.521 g (3.6 mmol) of 9-amino-1,4-dioxa-7-azaspiro[4.4]nonane, from Step 6 Example 208, for the spiro compound of that example, and heating at 40° C. instead of 65° C. for 288 hours instead of 48 hours, the crude product was obtained. The compound was dissolved in methylene chloride which was washed with 2×100 mL of water then dried over anhydrous sodium sulfate, then the solvent was removed by evaporation under vacuum. The product was purified with HPLC, eluting with 60% increasing to 65% methanol/water. The solvent was removed by evaporation under vacuum to afford 0.466 g of the title compound, NMR (CDCl3) d 1.12 (m, 4H), 1.40 (t, 3H, J=7.5 Hz), 3.45 (m, 5H), 3.62 (m, 1H), 3.78 (m, 2H), 3.84 (m, 1H), 3.98 (m, 1H), 4.07 (m, 4H), 4.38 (q, 2H, J=7.5 Hz), 7.83 (dd, 1H, J=15, 1.5 Hz), 8.50 (s, 1H).

Workup

  1. customheating at 40° C. instead of 65° C. for 288 hours instead of 48 hours
  2. customthe crude product was obtained
  3. washwas washed with 2×100 mL of water
  4. dry with materialthen dried over anhydrous sodium sulfate
  5. customthe solvent was removed by evaporation under vacuum
  6. customThe product was purified with HPLC
  7. washeluting with 60%
  8. temperatureincreasing to 65% methanol/water
  9. customThe solvent was removed by evaporation under vacuum

Sources & evidence

ORD record
ord-4dab493a3eae44809db305df9484b8a6
Source dataset
uspto-grants-1992_08
Patent number
US05137892

Reaction notes

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