Triethylamine → HCID 24752946, compound

HRID 561160Notes

Reaction equation

HRID 561160 reaction equation
[NH2:1][C:2]1[C:11]([F:12])=[C:10](F)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1.[N:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[NH:27][CH2:28][CH2:29][NH2:30].C(N(CC)CC)C.[NH4+].[Cl-]>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:30][CH2:29][CH2:28][NH:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][N:21]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:20])[C:5]([C:17]([OH:19])=[O:18])=[CH:6][N:7]2[CH:14]1[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 148802095-Amino-1-cyclopropyl-6,7-difluoro-1,4-dihydro-4-oxoquinoline-3-carboxylic acid

Product 1

HCID 24752946HCID 24752946, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-amino-1-cyclopropyl-6,7-difluoro-4-oxo-1,4-dihydroquinoline-3-carboxylic acid (300 mg, 1.07 mmol), N-2-pyridyl-1,2-ethanediamine (221 mg, 1.61 mmol) and triethylamine (0.224 mL, 1.61 mmol) in DMSO (5 mL) was stirred at 100° C. for 3 h. After the reaction mixture was cooled to room temperature, 10% aq. NH4Cl was added to neutralize and the suspension was stirred for 30 min. The resulting precipitate was collected by filtration in vacuo, washed with water and hot EtOH, dried to yield 5-amino-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (385 mg, 91%) as a colorless solid.

Workup

  1. filtrationThe resulting precipitate was collected by filtration in vacuo
  2. washwashed with water and hot EtOH
  3. customdried

Sources & evidence

ORD record
ord-eb98291cdb714512af88ba8b75978e7d
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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