N-hydroxy-2-pyridinecarboximidoyl chloride → 7-[cis-3-(2-Pyridyl)-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazol-5-yl]-1-cyclopropyl-8-methoxy-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

HRID 600735Notes

Reaction equation

HRID 600735 reaction equation
[OH:1][N:2]=[C:3](Cl)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[CH:11]1([N:14]2[C:23]3[C:18](=[CH:19][C:20]([F:31])=[C:21]([N:26]4[CH2:30][CH:29]=[CH:28][CH2:27]4)[C:22]=3[O:24][CH3:25])[C:17](=[O:32])[C:16]([C:33]([OH:35])=[O:34])=[CH:15]2)[CH2:13][CH2:12]1.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[N:5]1[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=1[C:3]1[C@@H:28]2[CH2:27][N:26]([C:21]3[C:22]([O:24][CH3:25])=[C:23]4[C:18]([C:17](=[O:32])[C:16]([C:33]([OH:35])=[O:34])=[CH:15][N:14]4[CH:11]4[CH2:12][CH2:13]4)=[CH:19][C:20]=3[F:31])[CH2:30][C@@H:29]2[O:1][N:2]=1

Participants

5

Reactant 3

HCID 421736N-hydroxy-2-pyridinecarboximidoyl chlorideHCID 516892Sodium BicarbonateHCID 575555521-Cyclopropyl-7-(2,5-dihydro-pyrrol-1-yl)-6-fluoro-8-methoxy-4-oxo-1,4-dihydro-quinoline-3-carboxylic acid

Product 1

HCID 689744027-[cis-3-(2-Pyridyl)-3a,4,6,6a-tetrahydropyrrolo[3,4-d]isoxazol-5-yl]-1-cyclopropyl-8-methoxy-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

Chloro oxime 2e (70 mg; 0.44 mmol), olefin 119 (100 mg; 0.29 mmol) and sodium bicarbonate (50 mg) in ethyl acetate (10 mL) were heated at reflux temperature overnight. The solid was filtered and the filtrate evaporated. The residue was triturated with methanol to yield acid 122.

Workup

  1. temperatureat reflux temperature overnight
  2. filtrationThe solid was filtered
  3. customthe filtrate evaporated
  4. customThe residue was triturated with methanol

Sources & evidence

ORD record
ord-d5839582b235447fbe5880d4ccced474
Source dataset
uspto-grants-2011_03
Patent number
US07902227B2

Reaction notes

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