Triethylamine → HCID 24752945, compound

HRID 561131Notes

Reaction equation

HRID 561131 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:19])[C:5]([C:16]([OH:18])=[O:17])=[CH:6][NH:7]2.[N:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[NH:26][CH2:27][CH2:28][NH2:29].C(N(CC)CC)C>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:29][CH2:28][CH2:27][NH:26][C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][N:20]=2)[C:9]([O:14][CH3:15])=[C:8]2[C:3]=1[C:4](=[O:19])[C:5]([C:16]([OH:18])=[O:17])=[CH:6][NH:7]2

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamine2×HCID 59002964HCID 59002964, compound

Product 1

HCID 24752945HCID 24752945, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 5-amino-6,7-difluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (400 mg, 1.48 mmol), N-2-pyridyl-1,2-ethanediamine (406 mg, 2.96 mmol) and triethylamine (0.410 mL, 2.94 mmol) in DMSO (2 mL) was stirred at 100° C. After 8 h, to the solution was added N-2-pyridyl-1,2-ethanediamine (102 mg, 0.744 mmol) and triethylamine (0.200 mL, 1.43 mmol) and stirred at 100° C. for another 8 h. The reaction mixture was poured into ice water and the resulting precipitate was removed by filtration, washed with ethanol. The resulting solid recrystallized by CH3CN, and dried to yield 5-amino-6-fluoro-1,4-dihydro-8-methoxy-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (132 mg, 23%) as a pale yellow solid.

Workup

  1. customthe resulting precipitate was removed by filtration
  2. washwashed with ethanol
  3. customThe resulting solid recrystallized by CH3CN
  4. customdried

Sources & evidence

ORD record
ord-ee91183259cd449b9e40766882002634
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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