Triethylamine → HCID 59002821, compound

HRID 561101Notes

Reaction equation

HRID 561101 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1.[CH3:23][N:24]([C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=1)[CH2:25][CH2:26][NH2:27].C(N(CC)CC)C>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:27][CH2:26][CH2:25][N:24]([CH3:23])[C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][N:29]=2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:22])[C:5]([C:19]([OH:21])=[O:20])=[CH:6][N:7]2[CH:16]1[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 105668945-Amino-1-cyclopropyl-6,7-difluoro-8-methoxy-1,4-dihydro-4-oxoquinoline-3-carboxylic acidHCID 18947459HCID 18947459, compound

Product 1

HCID 59002821HCID 59002821, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 5-amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (400 mg, 1.44 mmol), N-methyl-N-(2-pyridyl)-1,2-ethanediamine (326 mg, 2.16 mmol) and triethylamine (0.300 mL, 2.15 mmol) in anhydrous DMSO (6 mL) was stirred at 100° C. for 3 h. After cooling, the reaction mixture was poured into ice-water (50 mL), the resulting precipitate was collected by filtration and washed with water. The obtained solid was recrystallized from EtOH to give 5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-8-methoxy-7-[2-[methyl(2-pyridyl)amino]ethylamino]-4-oxoquinoline-3-carboxylic acid (303 mg, 48%) as yellow needles.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting precipitate was collected by filtration
  3. washwashed with water
  4. customThe obtained solid was recrystallized from EtOH

Sources & evidence

ORD record
ord-72ad8bf94c3b4adbbbe7f47d09c8b450
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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