Dimethylformamide → HCID 69958478, compound

HRID 1415960Notes

Reaction equation

HRID 1415960 reaction equation
CN(C)C=O.[CH2:6]([O:8][C:9]([NH:11][C:12]1[CH:13]=[C:14]([N:20]2[C:29]3[C:24](=[CH:25][C:26]([F:31])=[C:27](Cl)[N:28]=3)[C:23](=[O:32])[C:22]([C:33]([OH:35])=[O:34])=[CH:21]2)[C:15]([F:19])=[CH:16][C:17]=1[F:18])=[O:10])[CH3:7].[NH2:36][C@H:37]1[CH2:41][CH2:40][NH:39][CH2:38]1>C(O)C>[CH:37]([O:32][CH:23]([CH3:22])[CH3:24])([CH3:41])[CH3:38].[NH2:36][C@H:37]1[CH2:41][CH2:40][N:39]([C:27]2[N:28]=[C:29]3[C:24]([C:23](=[O:32])[C:22]([C:33]([OH:35])=[O:34])=[CH:21][N:20]3[C:14]3[C:15]([F:19])=[CH:16][C:17]([F:18])=[C:12]([NH:11][C:9]([O:8][CH2:6][CH3:7])=[O:10])[CH:13]=3)=[CH:25][C:26]=2[F:31])[CH2:38]1

Participants

6

Reactant 3

HCID 6228DimethylformamideHCID 1519351(3S)-(-)-3-AminopyrrolidineHCID 22440979HCID 22440979, compound

Product 2

HCID 7914Diisopropyl EtherHCID 69958478HCID 69958478, compoundYield 193%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

To 350 μl of N,N-dimethylformamide were added 68 mg of 1-(3-ethoxycarbonylamino-4,6-difluorophenyl)-7-chloro-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid and 70 mg of (3S)-3-aminopyrrolidine. The solution was stirred at 80° C. for 20 minutes. Then 0.5 ml of ethanol was added. The reaction solution was allowed to cool down whereupon the precipitate was collected by filtration and washed with ethanol and then diisopropyl ether to give 73 mg of the title compound.

Workup

  1. temperatureto cool down whereupon the precipitate
  2. filtrationwas collected by filtration
  3. washwashed with ethanol

Sources & evidence

ORD record
ord-c2bd8322baeb49c9ba93c2dde22246bd
Source dataset
uspto-grants-1999_06
Patent number
US05910498

Reaction notes

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