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

HRID 232500Notes

Reaction equation

HRID 232500 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:24]2[N:33]=[C:32]3[C:27]([C:28](=[O:47])[C:29]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:30][N:31]3[C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=3[F:41])=[CH:26][C:25]=2[F:48])=O)C=CC=CC=1.C(OCC)C>C(O)C>[NH2:3][CH:4]1[CH2:8][CH2:7][N:6]([C:24]2[N:33]=[C:32]3[C:27]([C:28](=[O:47])[C:29]([C:42]([O:44][CH2:45][CH3:46])=[O:43])=[CH:30][N:31]3[C:34]3[CH:39]=[CH:38][C:37]([F:40])=[CH:36][C:35]=3[F:41])=[CH:26][C:25]=2[F:48])[CH2:5]1

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 13849340Ethyl 7-benzenesulfinyl-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 83.8%

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, after which 300 mg of ethyl 7-benzenesulfinyl-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate was added thereto. The resulting mixture was subjected to reaction at room temperature for 3 hours, and to the reaction mixture was added 10 ml of diethyl ether, after which crystals were collected by filtration, and washed with 12 ml of water to obtain 230 mg (yield 83.8%) 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. customThe resulting mixture was subjected to reaction at room temperature for 3 hours
  3. filtrationafter which crystals were collected by filtration
  4. washwashed with 12 ml of water

Sources & evidence

ORD record
ord-9dc1872929904614bd787c08b8077c94
Source dataset
uspto-grants-1989_07
Patent number
US04851535

Reaction notes

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