Diethyl Ether → Ethyl 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 232501Notes

Reaction equation

HRID 232501 reaction equation
Cl.Cl.[NH2:3][CH:4]1[CH2:8][CH2:7][NH:6][CH2:5]1.C(N(CC)CC)C.C1(S([C:25]2[N:34]=[C:33]3[C:28]([C:29](=[O:48])[C:30]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:31][N:32]3[C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=3[F:42])=[CH:27][C:26]=2[F:49])(=O)=O)C=CC=CC=1.C(OCC)C>C(O)C>[NH2:3][CH:4]1[CH2:8][CH2:7][N:6]([C:25]2[N:34]=[C:33]3[C:28]([C:29](=[O:48])[C:30]([C:43]([O:45][CH2:46][CH3:47])=[O:44])=[CH:31][N:32]3[C:35]3[CH:40]=[CH:39][C:38]([F:41])=[CH:37][C:36]=3[F:42])=[CH:27][C:26]=2[F:49])[CH2:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 13849342Ethyl 7-benzenesulfonyl-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine 3-carboxylateHCID 162125963-Aminopyrrolidine dihydrochloride

Product 1

HCID 13667039Ethyl 7-(3-aminopyrrolidin-1-yl)-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,8-naphthyridine-3-carboxylateYield 86.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 3 ml of ethanol was suspended 120 mg of 3-aminopyrrolidine dihydrochloride, and 250 mg of triethylamine was added thereto to form a solution. Subsequently, 300 mg of ethyl 7-benzenesulfonyl-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate was added to the solution, and the resulting mixture was subjected to reaction at 45° to 50° C. for 4 hours. To the reaction mixture was added 10 ml of diethyl ether, and crystals were collected by filtration and washed with 12 ml of water to obtain 230 mg (yield 86.6%) of ethyl 7-(3-amino-1-pyrrolidinyl)-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate. The physical properties of this compound were identical with those of the compound obtained in Example 64.

Workup

  1. additionwas added
  2. customto form a solution
  3. customthe resulting mixture was subjected to reaction at 45° to 50° C. for 4 hours
  4. filtrationwere collected by filtration
  5. washwashed with 12 ml of water

Sources & evidence

ORD record
ord-12a386458f234364b1f2abe79f431980
Source dataset
uspto-grants-1989_07
Patent number
US04851535

Reaction notes

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