Dimethylformamide → HCID 15021561, compound

HRID 465386Notes

Reaction equation

HRID 465386 reaction equation
[CH:1]1([N:4]2[C:13]3[C:8](=[C:9]([NH2:17])[C:10]([F:16])=[C:11](F)[C:12]=3[F:14])[C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5]2)[CH2:3][CH2:2]1.[CH3:22][N:23]1[CH2:27][CH2:26][CH:25]([CH2:28][OH:29])[CH2:24]1.CN(C=O)C.[H-].[Na+]>C(O)(=O)C>[CH3:22][N:23]1[CH2:27][CH2:26][CH:25]([CH2:28][O:29][C:11]2[C:12]([F:14])=[C:13]3[C:8]([C:7](=[O:18])[C:6]([C:19]([OH:21])=[O:20])=[CH:5][N:4]3[CH:1]3[CH2:3][CH2:2]3)=[C:9]([NH2:17])[C:10]=2[F:16])[CH2:24]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 295970(1-methylpyrrolidin-3-yl)methanolHCID 139109475-Amino-1-cyclopropyl-6,7,8-trifluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid

Product 1

HCID 15021561HCID 15021561, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 596 mg of 1-cyclopropyl-5-amino-6,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid, 460 mg of 1-methyl-3-hydroxymethylpyrrolidine and 5 ml of DMF was added 262 mg of 55% sodium hydride while the former was stirred at room temperature. After the resultant mixture was stirred for 1 hour at room temperature, 360 mg of acetic acid was added and DMF was distilled off under reduced pressure. The residue was purified by chromatography on silica gel (chloroform/methanol: 3/1), followed by recrystallization from ethanol. The title compound was obtained as pale green powder (yield: 240 mg).

Workup

  1. distillationDMF was distilled off under reduced pressure
  2. customThe residue was purified by chromatography on silica gel (chloroform/methanol: 3/1)
  3. customfollowed by recrystallization from ethanol

Sources & evidence

ORD record
ord-f1026c59e1da400aaa581ced65fe9ef7
Source dataset
uspto-grants-1992_10
Patent number
US05153203

Reaction notes

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