Dimethyl Sulfoxide → HCID 10450969, compound

HRID 1975335Notes

Reaction equation

HRID 1975335 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11](F)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1.[CH2:20]1[C:22]2([CH2:27][NH:26][CH2:25][CH2:24][NH:23]2)[CH2:21]1.CS(C)=O>C(N(CC)CC)C>[CH:1]1([N:4]2[C:13]3[C:8](=[CH:9][C:10]([F:15])=[C:11]([N:26]4[CH2:27][C:22]5([CH2:20][CH2:21]5)[NH:23][CH2:24][CH2:25]4)[CH:12]=3)[C:7](=[O:16])[C:6]([C:17]([OH:19])=[O:18])=[CH:5]2)[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 679Dimethyl SulfoxideHCID 52104221-Cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 153380064,7-Diazaspiro[2.5]octane

Product 1

HCID 10450969HCID 10450969, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
120 °C

Procedure

200 mg of 1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid and 200 mg of crude 4,7-diazaspiro[2,5]octane 25 were added to 10 ml of dimethyl sulfoxide followed by the addition of 0.3 ml of triethylamine. The mixture was heated on a bath of 120° C. for 2 hours. The solvent was then removed under reduced pressure and the residue was subjected to silica gel column chromatography, eluting with chloroform-methanol-water=15:3:1 (v/v). The crude product obtained from the fraction containing the desired compound was recrystallized from ethanol-concentrated aqueous ammonia to give 160 mg of title compound 37.

Workup

  1. customThe solvent was then removed under reduced pressure
  2. washeluting with chloroform-methanol-water=15:3:1 (v/v)
  3. customThe crude product obtained from the fraction

Sources & evidence

ORD record
ord-e3f10b27cb60447693220a72fa13fbb3
Source dataset
uspto-grants-1994_02
Patent number
US05286723

Reaction notes

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