Methanesulfonic Acid → 8-(3-Amino-3-ethyl-1-azetidinyl)-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid methanesulphonate

HRID 743667Notes

Reaction equation

HRID 743667 reaction equation
[F:1][C:2]1[C:22](F)=[CH:21][C:5]2=[N:6][C:7]3[N:8]([CH:18]4[CH2:20][CH2:19]4)[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.[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].CS(O)(=O)=O.[NH2:34][C:35]1([CH2:39][CH3:40])[CH2:38][NH:37][CH2:36]1.CS(O)(=O)=O>C(O)C>[CH3:24][S:25]([OH:28])(=[O:27])=[O:26].[NH2:34][C:35]1([CH2:39][CH3:40])[CH2:38][N:37]([C:22]2[C:2]([F:1])=[CH:3][C:4]3[C:5]([CH:21]=2)=[N:6][C:7]2[N:8]([CH:18]4[CH2:19][CH2:20]4)[CH:9]=[C:10]([C:15]([OH:17])=[O:16])[C:11](=[O:14])[C:12]=2[CH:13]=3)[CH2:36]1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 148533411-Cyclopropyl-7,8-difluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acidHCID 194236433-Amino-3-ethylazetidine dimethanesulphonate

Product 1

HCID 867498358-(3-Amino-3-ethyl-1-azetidinyl)-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid methanesulphonateYield 19.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
80 °C

Procedure

8-(3-Amino-3-ethyl-1-azetidinyl)-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid methanesulphonate was prepared under the conditions of Example 15, but starting with 1.8 g of 7,8-difluoro-1-cyclopropyl-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid and 2.94 g of 3-amino-3-ethylazetidine dimethanesulphonate. After recrystallization in dimethylformamide, the product obtained, suspended in 20 cm3 of ethanol, is treated with 3.4 cm3 of a solution at a concentration of 9.6 g % of methanesulphonic acid in ethanol. The suspension is stirred for 5 minutes at approximately 80° C., cooled to a temperature in the region of 20° C., drained and washed with 3 times 10 cm3 of ethanol. 0.55 g of 8-(3-amino-3-ethyl-1-azetidinyl)-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]naphthyridine-3-carboxylic acid methanesulphonate is obtained in the form of a yellow solid, which decomposes at 248° C.

Workup

  1. custom8-(3-Amino-3-ethyl-1-azetidinyl)-1-cyclopropyl-7-fluoro-4-oxo-1,4-dihydrobenzo[b][1,8]-naphthyridine-3-carboxylic acid methanesulphonate was prepared under the conditions of Example 15
  2. customAfter recrystallization in dimethylformamide
  3. customthe product obtained
  4. temperaturecooled to a temperature in the region of 20° C.
  5. washwashed with 3 times 10 cm3 of ethanol

Sources & evidence

ORD record
ord-0629d9ea63a84e3794e2029ca65d9135
Source dataset
uspto-grants-1996_09
Patent number
US05556861

Reaction notes

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