Triethylamine → 8-Chloro-7-{4-[(cyclohexylamino)carbonyl]piperidin-1-yl}-1-cyclopropyl-n-(2,4-dichlorobenzyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamide

HRID 1011224

Reaction equation

HRID 1011224 reaction equation
[Cl:1][C:2]1[C:3](F)=[C:4]([F:28])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])=[O:16])[C:7]2=[O:27].[CH:30]1([NH:36][C:37]([CH:39]2[CH2:44][CH2:43][NH:42][CH2:41][CH2:40]2)=[O:38])[CH2:35][CH2:34][CH2:33][CH2:32][CH2:31]1.C(N(CC)CC)C>CS(C)=O>[Cl:1][C:2]1[C:3]([N:42]2[CH2:43][CH2:44][CH:39]([C:37]([NH:36][CH:30]3[CH2:31][CH2:32][CH2:33][CH2:34][CH2:35]3)=[O:38])[CH2:40][CH2:41]2)=[C:4]([F:28])[CH:5]=[C:6]2[C:11]=1[N:10]([CH:12]1[CH2:14][CH2:13]1)[CH:9]=[C:8]([C:15]([NH:17][CH2:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[Cl:26])=[O:16])[C:7]2=[O:27]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 12410238HCID 12410238, compoundHCID 577809783-Quinolinecarboxamide,8-chloro-1-cyclopropyl-n-[(2,4-dichlorophenyl)methyl]-6,7-difluoro-1,4-dihydro-4-oxo-

Product 1

HCID 577809288-Chloro-7-{4-[(cyclohexylamino)carbonyl]piperidin-1-yl}-1-cyclopropyl-n-(2,4-dichlorobenzyl)-6-fluoro-4-oxo-1,4-dihydroquinoline-3-carboxamideYield 10.5%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

200 mg (0.44 mmol) of the compound of Example 70A and 138 mg (0.66 mmol) of 4-(cyclohexylamino)carbonylpiperidine (for preparation see WO 2003031397) are heated with 91 μl (0.66 mmol) of triethylamine in 4 ml of DMSO at 120° C. for 7 h. After cooling, the entire reaction mixture is separated by preparative HPLC (method 6). 30 mg of the title compound are obtained.

Workup

  1. temperatureAfter cooling
  2. customthe entire reaction mixture
  3. customis separated by preparative HPLC (method 6)

Sources & evidence

ORD record
ord-b42459cec24e4bdf830f1a3db0db7fd8
Source dataset
uspto-grants-2011_07
Patent number
US07977349B2

Linked notes

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