Ethanol → 7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-3-(methylamino)quinolin-4(1H)-one

HRID 469237

Reaction equation

HRID 469237 reaction equation
[CH2:1](O)C.[NH2:4][C:5]1[C:14](=[O:15])[C:13]2[C:8](=[CH:9][C:10]([NH:17][CH:18]3[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]3)=[C:11]([F:16])[CH:12]=2)[N:7]([CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH:6]=1.N1(CO)C2C=CC=CC=2N=N1.[BH4-].[Na+]>O>[CH:18]1([NH:17][C:10]2[CH:9]=[C:8]3[C:13]([C:14](=[O:15])[C:5]([NH:4][CH3:1])=[CH:6][N:7]3[CH:24]([CH2:27][CH3:28])[CH2:25][CH3:26])=[CH:12][C:11]=2[F:16])[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1

Participants

6

Reactant 4

HCID 702EthanolHCID 2241691H-Benzotriazole-1-methanolHCID 4311764Sodium borohydrideHCID 666368863-amino-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one

Product 1

HCID 666369077-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-3-(methylamino)quinolin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 4 ml ethanol solution of 220 mg of 3-amino-7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoroquinolin-4(1H)-one was added 105 mg of 1H-1,2,3-benzotriazol-1-ylmethanol, followed by overnight stirring at room temperature. Next, 48 mg of sodium borohydride was added to the reaction mixture, followed by stirring for 3 hours. By adding water to the resulting reaction mixture and collecting the insoluble materials by filtration, 100 mg of 7-(cyclohexylamino)-1-(1-ethylpropyl)-6-fluoro-3-(methylamino)quinolin-4(1H)-one was obtained.

Workup

  1. stirringby stirring for 3 hours
  2. customto the resulting reaction mixture
  3. customcollecting the insoluble materials
  4. filtrationby filtration

Sources & evidence

ORD record
ord-f933c727abd14503998f8e75d67f83dd
Source dataset
uspto-grants-2014_01
Patent number
US08629126B2

Linked notes

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