Triethylamine → HCID 24754183, compound

HRID 561173Notes

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:25])[C:5]([C:22]([OH:24])=[O:23])=[CH:6][N:7]2[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[N:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[NH:32][CH2:33][CH2:34][NH2:35].C(N(CC)CC)C>CS(C)=O>[NH2:1][C:2]1[C:11]([F:12])=[C:10]([NH:35][CH2:34][CH2:33][NH:32][C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][N:26]=2)[CH:9]=[C:8]2[C:3]=1[C:4](=[O:25])[C:5]([C:22]([OH:24])=[O:23])=[CH:6][N:7]2[CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

Conditions

Temperature: 100 °C

Procedure

A suspension of 5-amino-6,7-difluoro-1,4-dihydro-4-oxo-1-(2-phenylethyl)-3-quinolinecarboxylic acid (101 mg, 0.292 mmol), 2-(2-pyridylamino)ethylamine (60.2 mg, 0.436 mmol), and triethylamine (60.7 μL, 0.435 mmol) in DMSO (1.5 mL) was stirred at 100° C. for 3 h. The reaction mixture was poured into ice-water and the resulting precipitates were collected by filtration. Recrystallization of the filtered precipitates from CH2Cl2-EtOH gave 5-amino-6-fluoro-1,4-dihydro-4-oxo-1-(2-phenylethyl)-7-[2-(2-pyridylamino)ethylamino]-3-quinolinecarboxylic acid (103 mg, 76%) as a pale brown powder.

Workup

customthe resulting precipitates
filtrationwere collected by filtration
customRecrystallization of the filtered
customprecipitates from CH2Cl2-EtOH

Sources & evidence

ORD record: ord-28c8c2b47e6d4238bb798ad514c23fd8
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063221B2

Reaction notes

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