Acetic Acid → HCID 24754254, compound

HRID 561159Notes

Reaction equation

HRID 561159 reaction equation
[NH2:1][C:2]1[C:11]([Cl: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.[N:23]1[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=1[NH:29][CH2:30][CH2:31][NH2:32].C(N(CC)CC)C.CC(O)=O>CS(C)=O>[NH2:1][C:2]1[C:11]([Cl:12])=[C:10]([NH:32][CH2:31][CH2:30][NH:29][C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][N:23]=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

6

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 410428N~1~-(Pyridin-2-yl)ethane-1,2-diamineHCID 59002917HCID 59002917, compound

Product 1

HCID 24754254HCID 24754254, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 5-amino-6-chloro-1-cyclopropyl-7-fluoro-1,4-dihydro-8-methoxy-4-oxoquinoline-3-carboxylic acid (180 mg, 0.551 mmol), N-2-pyridyl-1,2-ethanediamine (113 mg, 0.827 mmol) and triethylamine (0.115 mL, 0.827 mmol) in DMSO (5 mL) was stirred at 100° C. for 8 h. After the reaction mixture was poured into ice-water, AcOH was added to pH<3 and the resulting precipitate was collected by filtration in vacuo, washed successibly with water and hot EtOH, dried to yield 5-amino-6-chloro-1-cyclopropyl-1,4-dihydro-8-methoxy-4-oxo-7-[2-(2-pyridylamino)ethylamino]quinoline-3-carboxylic acid (179 mg, 73%) as a pale yellow solid.

Workup

  1. additionwas added to pH<3
  2. filtrationthe resulting precipitate was collected by filtration in vacuo
  3. washwashed successibly with water and hot EtOH
  4. customdried

Sources & evidence

ORD record
ord-d14a4bd7d9d14cedb0f45ca127f5afb6
Source dataset
uspto-grants-2011_11
Patent number
US08063221B2

Reaction notes

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