Triethylamine → Ethyl 7-(3-acetylamino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

HRID 1905917Notes

Reaction equation

HRID 1905917 reaction equation
C1(C)C=CC(S([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:28])[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][N:17]3[CH:20]3[CH2:22][CH2:21]3)=[CH:12][C:11]=2[F:29])(=O)=O)=CC=1.[C:31]([NH:34][CH:35]1[CH2:39][CH2:38][NH:37][CH2:36]1)(=[O:33])[CH3:32].C(N(CC)CC)C>C(O)C>[C:31]([NH:34][CH:35]1[CH2:39][CH2:38][N:37]([C:10]2[N:19]=[C:18]3[C:13]([C:14](=[O:28])[C:15]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:16][N:17]3[CH:20]3[CH2:21][CH2:22]3)=[CH:12][C:11]=2[F:29])[CH2:36]1)(=[O:33])[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 5227153-AcetamidopyrrolidineHCID 13456046Ethyl 7-(p-tolylsulfonyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate

Product 1

HCID 13456047Ethyl 7-(3-acetylamino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylateYield 80.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of ethyl 7-(p-tolylsulfonyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (800 mg), 3-acetylaminopyrrolidine (300 mg), triethylamine (236 mg), and ethanol (25 ml) was refluxed for 2 hours. After evaporation of the solvent under reduced pressure, the residual crude crystals were recrystallized from ethanol-isopropyl ether to give ethyl 7-(3-acetylamino-1-pyrrolidinyl)-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (600 mg), m.p. 246°-248° C.

Workup

  1. temperaturewas refluxed for 2 hours
  2. customAfter evaporation of the solvent under reduced pressure
  3. customthe residual crude crystals were recrystallized from ethanol-isopropyl ether

Sources & evidence

ORD record
ord-d29011742f7d492c8435ff864775754f
Source dataset
uspto-grants-1987_03
Patent number
US04649144

Reaction notes

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