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

HRID 246979
Notes
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Reaction equation

HRID 246979 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
ParticipantsProcedureWorkupSources & evidenceReaction notes

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-carboxylate
Yield 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-d7391d3c050e4d8c8a530440403e03ee
Source dataset
uspto-grants-1987_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04704459

Reaction notes

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