Water → HCID 9949920, compound

HRID 743636Notes

Reaction equation

HRID 743636 reaction equation
[F:1][C:2]1[C:20](F)=[CH:19][C:5]2=[N:6][C:7]3[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=3[CH:13]=[C:4]2[CH:3]=1.[NH2:22][CH:23]1[CH2:26][NH:25][CH2:24]1.O>CS(C)=O>[NH2:22][CH:23]1[CH2:26][N:25]([C:20]2[C:2]([F:1])=[CH:3][C:4]3[C:5]([CH:19]=2)=[N:6][C:7]2[N:8]([CH3:18])[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=2[CH:13]=3)[CH2:24]1

Participants

5

Reactant 3

HCID 962WaterHCID 1516506Azetidin-3-amineHCID 11197026HCID 11197026, compound

Product 1

HCID 9949920HCID 9949920, compoundYield 51.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
95 °C

Procedure

A suspension of 1.16 g of 7,8-difluoro-1-methyl-4-oxo-l,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 1.38 g of 3-aminoazetidine in 15 cm3 of dimethyl sulphoxide is heated with stirring to a temperature in the region of 95° C. for 6 hours. After cooling to approximately 20° C., 100 cm3 of water are added to the reaction mixture. The insoluble matter is drained, washed with 3 times 20 cm3 of water, taken up with 100 cm3 of water and treated with 4 cm3 of N methanesulphonic acid. After removal of some slight insoluble matter by filtration through diatomaceous silica and addition of 4 cm3 of N aqueous sodium hydroxide, the suspension obtained is concentrated under reduced pressure (20 kPa) at a temperature in the region of 60°C. to a volume of approximately 80 cm3. The insoluble matter is drained, washed with 100 cm3 of water and 100 cm3 of ethanol and recrystallized in 150 cm3 of dimethylformamide. 0.7 g of 8-(3-amino-1-azetidinyl)-7-fluoro-1-methyl-4-oxo1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid is obtained in the form of a yellow solid, which decomposes at 358° C.

Workup

  1. temperatureis heated
  2. temperatureAfter cooling to approximately 20° C.
  3. washwashed with 3 times 20 cm3 of water
  4. additiontreated with 4 cm3 of N methanesulphonic acid
  5. customAfter removal of some slight insoluble matter
  6. filtrationby filtration
  7. additionthrough diatomaceous silica and addition of 4 cm3 of N aqueous sodium hydroxide
  8. customthe suspension obtained
  9. concentrationis concentrated under reduced pressure (20 kPa) at a temperature in the region of 60°C. to a volume of approximately 80 cm3
  10. washwashed with 100 cm3 of water and 100 cm3 of ethanol
  11. customrecrystallized in 150 cm3 of dimethylformamide

Sources & evidence

ORD record
ord-065c923d73d04bc39adf3f6ba68c4c89
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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